Conditions | Yield |
---|---|
With trichlorophosphate at 115℃; for 16h; | 100% |
With trichlorophosphate at 115℃; for 16h; | 100% |
With trichlorophosphate for 18h; Heating / reflux; | 96% |
Conditions | Yield |
---|---|
With pyridine; tetrachloromethane; titanium(IV) oxide; vanadia; tungsten(VI) oxide; tin(IV) oxide In N,N-dimethyl-formamide at 120 - 230℃; under 2250.23 - 6000.6 Torr; for 32h; Solvent; Temperature; Pressure; Reagent/catalyst; | 99.1% |
Conditions | Yield |
---|---|
With trichlorophosphate for 2.5h; Heating / reflux; | 99% |
With N-ethyl-N,N-diisopropylamine; trichlorophosphate at 110℃; for 3h; | 98.4% |
With N-ethyl-N,N-diisopropylamine; trichlorophosphate at 90℃; for 6h; | 95% |
bis(trichloromethyl) carbonate
anthranilic acid nitrile
2,4-dichloroquinazoline
Conditions | Yield |
---|---|
Stage #1: bis(trichloromethyl) carbonate With triethylamine; Triphenylphosphine oxide In chlorobenzene at 20℃; for 0.5h; Cooling with ice; Stage #2: anthranilic acid nitrile In chlorobenzene at 120℃; for 6h; | 95% |
Stage #1: bis(trichloromethyl) carbonate With triethylamine; Triphenylphosphine oxide In chlorobenzene at 0℃; for 0.5h; Stage #2: anthranilic acid nitrile In chlorobenzene at 120℃; for 5h; | 45% |
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine; trichlorophosphate at 100℃; for 4h; Sealed tube; | 93% |
3-(hydroxyimino)indolin-2-one
2,4-dichloroquinazoline
Conditions | Yield |
---|---|
With bis(trichloromethyl) carbonate; Tris(4-methoxyphenyl)phosphine oxide In chlorobenzene at 120℃; for 3h; Mechanism; Reagent/catalyst; | 93% |
Conditions | Yield |
---|---|
With trichlorophosphate at 80 - 85℃; for 0.5h; | 90% |
Conditions | Yield |
---|---|
With 1-Methylpyrrolidine; trichlorophosphate at 20 - 25℃; for 0.5h; | 90% |
N-tert-butyl-pyrrolidine
1,2,3,4-tetrahydro-quinazoline-2,4-dione
A
2,4-dichloroquinazoline
Conditions | Yield |
---|---|
With trichlorophosphate at 80 - 85℃; for 0.333333h; | A 88.5% B n/a |
anthranilic acid nitrile
trichloromethyl chloroformate
2,4-dichloroquinazoline
Conditions | Yield |
---|---|
In acetonitrile at 130℃; for 12h; | 86% |
Conditions | Yield |
---|---|
With trichlorophosphate at 80 - 85℃; for 0.333333h; | A 84.6% B n/a |
2,4-dichloroquinazoline
Conditions | Yield |
---|---|
With N,N-dimethyl-formamide; trichlorophosphate | 80% |
1-Methylpyrrolidine
1,2,3,4-tetrahydro-quinazoline-2,4-dione
A
2,4-dichloroquinazoline
B
4-chloro-2-quinazoline
Conditions | Yield |
---|---|
With trichlorophosphate at 80 - 85℃; for 0.333333h; | A 3.3% B 77.3% |
With trichlorophosphate at 80 - 85℃; for 0.333333h; | A 3.3% B 77.3% |
With trichlorophosphate at 20 - 25℃; for 0.166667h; | A 12.7% B 70.5% |
2,4-dioxo-1,2,3,4-tetrahydroquinoline
2,4-dichloroquinazoline
Conditions | Yield |
---|---|
Stage #1: 2,4-dioxo-1,2,3,4-tetrahydroquinoline With trichlorophosphate for 48h; Reflux; Stage #2: With water at 30℃; | 71% |
1,2,3,4-tetrahydro-quinazoline-2,4-dione
A
2,4-dichloroquinazoline
B
4-chloro-2-quinazoline
Conditions | Yield |
---|---|
With 1-methyl-pyrrolidin-2-one; trichlorophosphate at 20 - 25℃; for 0.166667h; | A 12.7% B 70.5% |
N-propylpyrrolidine
1,2,3,4-tetrahydro-quinazoline-2,4-dione
A
2,4-dichloroquinazoline
B
4-chloro-2-(N-propyl-4-chlorobutylamino)quinazoline
Conditions | Yield |
---|---|
With trichlorophosphate at 80 - 85℃; for 0.333333h; | A 19.5% B 59.4% |
With trichlorophosphate at 80 - 85℃; for 0.333333h; | A 19.5% B 59.4% |
1-ethylpyrrolidine
1,2,3,4-tetrahydro-quinazoline-2,4-dione
A
2,4-dichloroquinazoline
B
4-chloro-2-(N-ethyl-4-chlorobutylamino)quinazoline
Conditions | Yield |
---|---|
With trichlorophosphate at 80 - 85℃; for 0.333333h; | A 17.9% B 58.7% |
With trichlorophosphate at 80 - 85℃; for 0.333333h; | A 17.9% B 58.7% |
1-butylpyrrolidine
1,2,3,4-tetrahydro-quinazoline-2,4-dione
A
2,4-dichloroquinazoline
B
4-chloro-2-(N-butyl-4-chlorobutylamino)quinazoline
Conditions | Yield |
---|---|
With trichlorophosphate at 80 - 85℃; for 0.333333h; | A 48.5% B 34.7% |
With trichlorophosphate at 80 - 85℃; for 0.333333h; | A 48.5% B 34.7% |
N-methylcyclohexylamine
1,2,3,4-tetrahydro-quinazoline-2,4-dione
A
2,4-dichloroquinazoline
B
(5-Chloro-pentyl)-(4-chloro-quinazolin-2-yl)-methyl-amine
Conditions | Yield |
---|---|
With trichlorophosphate at 80 - 85℃; for 0.333333h; | A 41.9% B 28.2% |
Conditions | Yield |
---|---|
With phosphorus pentachloride at 160 - 170℃; im Rohr; |
1-Methylpyrrolidine
1,2,3,4-tetrahydro-quinazoline-2,4-dione
A
2-chloro-4(3H)-quinazolinone
B
2,4-dichloroquinazoline
C
4-chloro-2-quinazoline
D
2--4(3H)-quinazoline
Conditions | Yield |
---|---|
With trichlorophosphate Product distribution; Mechanism; ratio of products vs. conditions; |
2,4-dichloroquinazoline
Conditions | Yield |
---|---|
With phosphorus pentachloride; phosphorus trichloride at 150 - 160℃; im Rohr; | |
With phosphorus pentachloride; trichlorophosphate |
3-methyl-2,4(1H,3H)-quinazolinedione
phosphorus pentachloride
2,4-dichloroquinazoline
Conditions | Yield |
---|---|
at 160 - 170℃; im Rohr; |
phosphorus pentachloride
1,2,3,4-tetrahydro-quinazoline-2,4-dione
trichlorophosphate
2,4-dichloroquinazoline
phosphorus pentachloride
1,2,3,4-tetrahydro-quinazoline-2,4-dione
phosphorus trichloride
2,4-dichloroquinazoline
Conditions | Yield |
---|---|
at 150 - 160℃; im Rohr; |
N-(2-Cyanophenyl)-2,2,2-trifluoroacetamide
2,4-dichloroquinazoline
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: aq. K2CO3 / methanol / 12 h / 20 °C 2: 86 percent / acetonitrile / 12 h / 130 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: dimethylformamide / 0.5 h / 20 °C 2: dimethylformamide / 0.5 h / 100 °C 3: aq. K2CO3 / methanol / 12 h / 20 °C 4: 86 percent / acetonitrile / 12 h / 130 °C View Scheme |
2,2,2-trifluoro-N-(2-iodophenyl)acetamide
2,4-dichloroquinazoline
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: dimethylformamide / 0.5 h / 100 °C 2: aq. K2CO3 / methanol / 12 h / 20 °C 3: 86 percent / acetonitrile / 12 h / 130 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: ICl / dimethylformamide / 0.5 h / 20 °C 2: dimethylformamide / 0.5 h / 20 °C 3: dimethylformamide / 0.5 h / 100 °C 4: aq. K2CO3 / methanol / 12 h / 20 °C 5: 86 percent / acetonitrile / 12 h / 130 °C View Scheme |
2,4-dichloroquinazoline
2-chloro-quinazolin-4-ylamine
Conditions | Yield |
---|---|
With ammonia In methanol at 20℃; Substitution; | 100% |
With ammonium hydroxide at 20℃; for 28.5h; | 96% |
With ammonia In tetrahydrofuran; water at 20℃; | 72% |
1-methyl-piperazine
2,4-dichloroquinazoline
2-chloro-4-(4-methylpiperazin-1-yl)quinazoline
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In ethyl acetate at 0 - 20℃; for 1.5h; | 100% |
Stage #1: 1-methyl-piperazine; 2,4-dichloroquinazoline In tetrahydrofuran for 3.5h; Stage #2: With sodium hydroxide In tetrahydrofuran; dichloromethane; water | 96% |
With sodium carbonate In ethanol Heating; | 87% |
In tetrahydrofuran at 20℃; Condensation; |
2,4-dichloroquinazoline
3-methyl-5-aminopyrazole
2-chloro-N-(5-methyl-1H-pyrazol-3-yl)quinazolin-4-amine
Conditions | Yield |
---|---|
With triethylamine In ethanol at 20℃; | 100% |
With triethylamine In ethanol at 20℃; for 3h; | |
In ethanol |
2,4-dichloroquinazoline
N-(3-aminophenyl)cyclopropanesulfonamide
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol for 16h; Reflux; | 100% |
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol for 16h; Reflux; | 100% |
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran | 100% |
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran | 100% |
2,4-dichloroquinazoline
4-(naphthalene-2-yl)phenylboronic acid pinacol ester
C24H15ClN2
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene at 100℃; for 5h; | 99.9% |
Conditions | Yield |
---|---|
Stage #1: TETRAHYDROFURFURYLAMINE With triethylamine In methanol at 0℃; for 0.166667h; Inert atmosphere; Stage #2: 2,4-dichloroquinazoline In methanol; dichloromethane at 0 - 20℃; for 0.5h; Inert atmosphere; | 99% |
Stage #1: TETRAHYDROFURFURYLAMINE With triethylamine In methanol at 0℃; for 0.166667h; Inert atmosphere; Stage #2: 2,4-dichloroquinazoline In methanol; dichloromethane at 0 - 20℃; for 0.5h; Inert atmosphere; | 99% |
With sodium acetate In tetrahydrofuran; water at 65℃; | 82% |
With sodium hydroxide 1.) THF, 30 min, 2.) THF, 30 min; Multistep reaction; | |
With sodium acetate In tetrahydrofuran; water at 60℃; |
2,4-dichloroquinazoline
4-chloro-3-ethoxyphenylamine
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol for 18h; Reflux; | 99% |
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol for 18h; Reflux; | 99% |
Conditions | Yield |
---|---|
Stage #1: 2,4-dichloroquinazoline With sodium hydride at 17 - 24℃; for 4h; Inert atmosphere; Stage #2: With acetic acid In water at 21 - 24℃; Inert atmosphere; | 98.4% |
With sodium hydroxide In tetrahydrofuran; water | 96% |
With sodium hydroxide In tetrahydrofuran at 20℃; Inert atmosphere; | 91% |
1-(2-aminoethyl)pyrrolidine
2,4-dichloroquinazoline
2-chloro-N-<2-(1-pyrrolidinyl)ethyl>-4-quinazolinamine
Conditions | Yield |
---|---|
In diethyl ether at 20℃; for 12h; | 98% |
With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 18h; | 65% |
In diethyl ether for 1.5h; | 56% |
Conditions | Yield |
---|---|
With sodium acetate In tetrahydrofuran; water at 60℃; for 0.75h; | 98% |
With sodium acetate In tetrahydrofuran; water at 60℃; for 0.75h; | 98% |
2,4-dichloroquinazoline
glycine ethyl ester hydrochloride
methyl-2-(2-chloroquinazolin-4-ylamino)acetate
Conditions | Yield |
---|---|
With triethylamine In ethanol at 70℃; for 16h; | 98% |
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran at 20℃; | 97% |
With triethylamine In tetrahydrofuran for 0.5h; Reflux; | 92% |
With triethylamine In tetrahydrofuran at 60℃; for 1h; | 88% |
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol Substitution; Heating; | 97% |
With sodium acetate In tetrahydrofuran; water at 65℃; | 94% |
With triethylamine In tetrahydrofuran at 60℃; | 89% |
orcinol
2,4-dichloroquinazoline
3,5-bis(2-chloroquinazolin-4-yloxy)toluene
Conditions | Yield |
---|---|
With 18-crown-6 ether; potassium carbonate In acetone at 20℃; for 48h; Inert atmosphere; regioselective reaction; | 97% |
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran at 20℃; Inert atmosphere; | 97% |
Stage #1: 3-Aminomethylpyridine With triethylamine In tetrahydrofuran at 20℃; for 0.166667h; Stage #2: 2,4-dichloroquinazoline In tetrahydrofuran at 20℃; | 92.3% |
With triethylamine In tetrahydrofuran at 20℃; |
Conditions | Yield |
---|---|
With methanol at 20℃; for 48h; | 96% |
In methanol at 20℃; for 48h; | 96% |
With methanol; phenol |
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 75℃; | 95.5% |
2,4-dichloroquinazoline
4-methoxy-aniline
2-chloro-N-(4-methoxyphenyl)quinazolin-4-amine
Conditions | Yield |
---|---|
With sodium acetate In tetrahydrofuran; water at 65℃; for 1h; | 95% |
With hydrogenchloride In water; isopropyl alcohol at 20℃; | 77% |
With triethylamine In tetrahydrofuran at 30℃; | 69.2% |
With sodium acetate In tetrahydrofuran; water | 43% |
2,4-dichloroquinazoline
4-phenoxyanilin
(2-chloro-quinazolin-4-yl)-(4-phenoxy-phenyl)-amine
Conditions | Yield |
---|---|
With sodium acetate In tetrahydrofuran; water at 60℃; | 95% |
2,4-dichloroquinazoline
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; | 95% |
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; | 67% |
2-pyridin-3-ylethylamine
2,4-dichloroquinazoline
Conditions | Yield |
---|---|
Stage #1: 2-pyridin-3-ylethylamine With triethylamine In tetrahydrofuran at 20℃; for 0.166667h; Stage #2: 2,4-dichloroquinazoline In tetrahydrofuran at 20℃; | 94.3% |
2,4-dichloroquinazoline
2-aminomethylpyrazine
Conditions | Yield |
---|---|
Stage #1: 2-aminomethylpyrazine With triethylamine In tetrahydrofuran at 20℃; for 0.166667h; Stage #2: 2,4-dichloroquinazoline In tetrahydrofuran at 20℃; | 94.2% |
With triethylamine In tetrahydrofuran at 20℃; |
2,4-dichloroquinazoline
dimethyl amine
2-chloro-N,N-dimethylquinazolin-4-amine
Conditions | Yield |
---|---|
In tetrahydrofuran; water at 20℃; for 1.33333h; | 94% |
In tetrahydrofuran; water at 20℃; for 1.33333h; | 94% |
In tetrahydrofuran; water at 4 - 20℃; for 1.33333h; | 94% |
With triethylamine In water; N,N-dimethyl-formamide at 20℃; Ice cooling; | |
With sodium acetate In tetrahydrofuran; water | 0.037 g |
2,4-dichloroquinazoline
methylamine
2-chloro-4-(N-methylamino)quinazoline
Conditions | Yield |
---|---|
In tetrahydrofuran; water at 20℃; for 0.666667h; | 94% |
With sodium acetate In tetrahydrofuran; water at 65℃; | 92% |
With N-ethyl-N,N-diisopropylamine In ethanol at 20℃; for 4.5h; Inert atmosphere; | 91% |
IUPAC Name: 2,4-Dichloroquinazoline
Following is the structure of Quinazoline,2,4-dichloro- (CAS NO.607-68-1):
Empirical Formula: C8H4Cl2N2
Molecular Weight: 199.0368
Index of Refraction: 1.67
Molar Refractivity: 50.06 cm3
Molar Volume: 133.8 cm3
Density: 1.486 g/cm3
Flash Point: 145.4 °C
Surface Tension: 59 dyne/cm
Enthalpy of Vaporization: 49.1 kJ/mol
Boiling Point of Quinazoline,2,4-dichloro- (CAS NO.607-68-1): 273.3 °C at 760 mmHg
Vapour Pressure of Quinazoline,2,4-dichloro- (CAS NO.607-68-1): 0.00968 mmHg at 25 °C
Canonical SMILES: C1=CC=C2C(=C1)C(=NC(=N2)Cl)Cl
InChI: InChI=1S/C8H4Cl2N2/c9-7-5-3-1-2-4-6(5)11-8(10)12-7/h1-4H
InChIKey: TUQSVSYUEBNNKQ-UHFFFAOYSA-N
Quinazoline,2,4-dichloro- , its cas register number is 607-68-1. It also can be called 2,4-Dichloroquinazoline .
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