Conditions | Yield |
---|---|
With nitric acid; sodium nitrite at 10℃; |
N-Methyl-N'-nitro-N-nitrosoguanidine
(2E,4E)-5-Bromo-2,4-dimethyl-penta-2,4-dienoic acid
(2E,4E)-5-bromo-2,4-dimethyl-penta-2,4-dienoic acid methyl ester
Conditions | Yield |
---|---|
Stage #1: N-Methyl-N'-nitro-N-nitrosoguanidine With potassium hydroxide In diethyl ether at 0℃; for 0.25h; Stage #2: (2E,4E)-5-Bromo-2,4-dimethyl-penta-2,4-dienoic acid In diethyl ether | 99% |
N-Methyl-N'-nitro-N-nitrosoguanidine
C17H21FO3
methyl 2-(9-(4-fluorophenyl)-3-hydroxybicyclo[3.3.1]nonan-9-yl)acetate
Conditions | Yield |
---|---|
Stage #1: N-Methyl-N'-nitro-N-nitrosoguanidine With potassium hydroxide In diethyl ether; water at 0℃; for 0.0833333h; Stage #2: C17H21FO3 In diethyl ether; dichloromethane at 0℃; for 0.166667h; | 99% |
N-Methyl-N'-nitro-N-nitrosoguanidine
5-benzoylaminopentanoic acid
methyl N-benzoyl-5-aminopentanoate
Conditions | Yield |
---|---|
With sodium hydroxide In methanol; diethyl ether at 0℃; | 99% |
N-Methyl-N'-nitro-N-nitrosoguanidine
trans-methyl 4-(4-bromophenyl)but-2-enoate
Conditions | Yield |
---|---|
Stage #1: N-Methyl-N'-nitro-N-nitrosoguanidine With potassium hydroxide In diethyl ether at 0℃; for 0.25h; Stage #2: trans-methyl 4-(4-bromophenyl)but-2-enoate With palladium diacetate In tetrahydrofuran; diethyl ether at 20℃; for 1h; | 98% |
N-Methyl-N'-nitro-N-nitrosoguanidine
Conditions | Yield |
---|---|
With potassium hydroxide In diethyl ether; ethanol; water for 0.166667h; Inert atmosphere; | 98% |
N-Methyl-N'-nitro-N-nitrosoguanidine
Mrz 2/138
Conditions | Yield |
---|---|
In diethyl ether; water at 22℃; for 1.5h; | 96.5% |
In diethyl ether; water at 20 - 22℃; for 0.5h; | 96.5% |
N-Methyl-N'-nitro-N-nitrosoguanidine
Conditions | Yield |
---|---|
Stage #1: N-Methyl-N'-nitro-N-nitrosoguanidine With palladium diacetate; potassium hydroxide In diethyl ether; water at 0℃; for 0.333333h; Stage #2: (E)-methyl 4-(4-((3-phenoxybenzyl)oxy)bicyclo[2.2.1]heptan-1-yl)but-2-enoate With palladium diacetate In tetrahydrofuran at 0 - 20℃; for 1h; | 95% |
N-Methyl-N'-nitro-N-nitrosoguanidine
(2E)-N-benzylbut-2-enamide
Conditions | Yield |
---|---|
Stage #1: N-Methyl-N'-nitro-N-nitrosoguanidine With water; potassium hydroxide In diethyl ether at 0℃; for 0.25h; Stage #2: (2E)-N-benzylbut-2-enamide With palladium diacetate In tetrahydrofuran; diethyl ether at 20℃; for 1h; | 94% |
N-Methyl-N'-nitro-N-nitrosoguanidine
Conditions | Yield |
---|---|
With sodium hydroxide In diethyl ether at 0℃; | 94% |
Conditions | Yield |
---|---|
In methanol; water at 80℃; for 2h; | 93% |
N-Methyl-N'-nitro-N-nitrosoguanidine
Conditions | Yield |
---|---|
Stage #1: N-Methyl-N'-nitro-N-nitrosoguanidine With water; potassium hydroxide In diethyl ether at 0℃; for 0.333333h; Stage #2: (E)-methyl-cis-3-(3-(4-bromophenyl)cyclobutyl)acrylate With palladium diacetate In tetrahydrofuran; diethyl ether at 0 - 20℃; for 1h; | 92% |
N-Methyl-N'-nitro-N-nitrosoguanidine
Conditions | Yield |
---|---|
Stage #1: N-Methyl-N'-nitro-N-nitrosoguanidine With potassium hydroxide In diethyl ether; water at -78 - 0℃; for 0.5h; Stage #2: (E)-5-(4-bromophenyl)pent-2-enoic acid ethyl ester With palladium diacetate In diethyl ether; water at 0 - 20℃; Stage #3: With acetic acid In diethyl ether at 20℃; for 0.5h; | 91% |
Conditions | Yield |
---|---|
Stage #1: N-Methyl-N'-nitro-N-nitrosoguanidine; (4-amino-furazan-3-yl)-acetic acid hydrazide In methanol; water for 2h; Heating; Stage #2: With potassium hydroxide In water for 2h; Stage #3: With nitric acid In water at 50℃; pH=3; | 90% |
Conditions | Yield |
---|---|
In sodium hydroxide solvation of 16 g NaOH in 600 ml H2O and addition of 44.1 g of the guanidine under stirring at 0°C within 10 minutes, shaking for another 20 minutes and addition of 36 ml concentrated HNO3 in 150 ml H2O and 51 g AgNO3 in 150 ml H2O;; precipitation; washing with hot H2O;; | 89.4% |
N-Methyl-N'-nitro-N-nitrosoguanidine
3-methyl-4-(1-methyl-7-oxo-3-(pyridin-2-yl)-1,4,5,6,7,8-hexahydrocyclohepta[c]pyrazol-4-yl)benzoic acid
methyl 3-methyl-4-(1-methyl-7-oxo-3-(pyridin-2-yl)-1,4,5,6,7,8-hexahydrocyclohepta[c]pyrazol-4-yl)benzoate
Conditions | Yield |
---|---|
With potassium hydroxide In tetrahydrofuran; diethyl ether; water at 0℃; Inert atmosphere; | 88% |
N-Methyl-N'-nitro-N-nitrosoguanidine
Conditions | Yield |
---|---|
Stage #1: N-Methyl-N'-nitro-N-nitrosoguanidine With potassium hydroxide In diethyl ether; water at 0℃; for 0.25h; Stage #2: (E)-methyl 5-(4-bromophenyl)pent-2-enoate With palladium diacetate In tetrahydrofuran; diethyl ether; water at 20℃; for 1h; | 88% |
tert-butyl (3R,5R,6S)-3-(2-methylprop-2-enyl)-2-oxo-5,6-diphenylmorpholine-4-carboxylate
N-Methyl-N'-nitro-N-nitrosoguanidine
tert-butyl (3R,5R,6S)-3-[(1-methylcyclopropyl)methyl]-2-oxo-5,6-diphenylmorpholine-4-carboxylate
Conditions | Yield |
---|---|
Stage #1: N-Methyl-N'-nitro-N-nitrosoguanidine With potassium hydroxide In diethyl ether; water at 0℃; for 0.0833333h; Stage #2: tert-butyl (3R,5R,6S)-3-(2-methylprop-2-enyl)-2-oxo-5,6-diphenylmorpholine-4-carboxylate; palladium diacetate In tetrahydrofuran; diethyl ether at 0℃; | 86% |
N-Methyl-N'-nitro-N-nitrosoguanidine
Conditions | Yield |
---|---|
With water In methanol for 2h; Heating; | 86% |
Conditions | Yield |
---|---|
Stage #1: N-Methyl-N'-nitro-N-nitrosoguanidine; furoxancarboxylic acid hydrazide In methanol; water for 2h; Heating; Stage #2: With potassium hydroxide In methanol; water for 2h; Stage #3: With nitric acid at 50℃; pH=3; | 85% |
N-Methyl-N'-nitro-N-nitrosoguanidine
(2E)-N-benzylbut-2-enamide
Conditions | Yield |
---|---|
Stage #1: N-Methyl-N'-nitro-N-nitrosoguanidine With potassium hydroxide In diethyl ether; water at 20℃; for 0.166667h; Stage #2: (2E)-N-benzylbut-2-enamide; palladium diacetate In tetrahydrofuran; diethyl ether at 20℃; for 1h; | 83% |
Stage #1: N-Methyl-N'-nitro-N-nitrosoguanidine With potassium hydroxide In diethyl ether; water at -78 - 20℃; for 0.0833333h; Stage #2: (2E)-N-benzylbut-2-enamide; palladium diacetate In tetrahydrofuran; diethyl ether at 20℃; for 1h; |
N-Methyl-N'-nitro-N-nitrosoguanidine
ethyl (E)-3-(3-fluoro-4-methoxyphenyl)acrylate
2-(3-fluoro-4-methoxyphenyl)cyclopropanecarboxylic acid ethyl ester
Conditions | Yield |
---|---|
Stage #1: N-Methyl-N'-nitro-N-nitrosoguanidine With water; potassium hydroxide In diethyl ether at 0℃; for 0.0333333h; Stage #2: ethyl (E)-3-(3-fluoro-4-methoxyphenyl)acrylate; palladium diacetate In diethyl ether at 0 - 5℃; for 4h; Stage #3: With acetic acid In diethyl ether | 83% |
Stage #1: N-Methyl-N'-nitro-N-nitrosoguanidine With potassium hydroxide In diethyl ether; water at 0℃; Stage #2: ethyl (E)-3-(3-fluoro-4-methoxyphenyl)acrylate; palladium diacetate In diethyl ether; water at 0 - 5℃; Stage #3: With acetic acid In diethyl ether; water | 83% |
diazomethane
N-Methyl-N'-nitro-N-nitrosoguanidine
3-(2-isopropylphenyl)propanoyl chloride
1-diazo-4-(2-isopropylphenyl)butan-2-one
Conditions | Yield |
---|---|
In dichloromethane | 82% |
N-[5-(N-4-toluenesulfonyl-amino)pyrimidin-4-yl]-L-4-(N,N-dimethylcarbarnyloxy)phenylalanine tert-butyl ester
N-Methyl-N'-nitro-N-nitrosoguanidine
N-[5-(N-methyl-N-4-toluenesulfonylamino)pyrimidin-4-yl]-L-4-(N,N-dimethylcarbarnyloxy)phenylalanine tert-butyl ester
Conditions | Yield |
---|---|
Stage #1: N-Methyl-N'-nitro-N-nitrosoguanidine With sodium hydroxide In diethyl ether at 0℃; for 0.416667h; Stage #2: Stage #3: N-[5-(N-4-toluenesulfonyl-amino)pyrimidin-4-yl]-L-4-(N,N-dimethylcarbarnyloxy)phenylalanine tert-butyl ester In diethyl ether; dichloromethane at 0℃; for 0.25h; | 82% |
N-Methyl-N'-nitro-N-nitrosoguanidine
Conditions | Yield |
---|---|
Stage #1: N-Methyl-N'-nitro-N-nitrosoguanidine; 3-Aminofurazan-4-carboxylic acid hydrazide In methanol; water for 2h; Heating; Stage #2: With potassium hydroxide In water for 2h; Stage #3: With nitric acid In water at 50℃; pH=3; | 82% |
N-Methyl-N'-nitro-N-nitrosoguanidine
Conditions | Yield |
---|---|
With nitric acid; potassium hydroxide In water Reflux; | 82% |
N-Methyl-N'-nitro-N-nitrosoguanidine
Conditions | Yield |
---|---|
Stage #1: N-Methyl-N'-nitro-N-nitrosoguanidine With potassium hydroxide In diethyl ether; water at 0℃; for 0.166667h; Stage #2: C29H38BrN3O5 In diethyl ether; dichloromethane; water at 0℃; for 0.5h; | 81% |
N-Methyl-N'-nitro-N-nitrosoguanidine
(2S,3R)-4-benzyl 1-tert-butyl 2-allyl-3-(3,3,3-trifluoropropyl)succinate
(2R,3S)-1-benzyl 4-tert-butyl 3-(cyclopropylmethyl)-2-(3,3,3-5 trifluoropropyl)succinate
Conditions | Yield |
---|---|
With palladium diacetate; potassium hydroxide In diethyl ether; water at 0℃; for 3h; | 81% |
Stage #1: N-Methyl-N'-nitro-N-nitrosoguanidine With potassium hydroxide In diethyl ether at 0℃; Stage #2: (2S,3R)-4-benzyl 1-tert-butyl 2-allyl-3-(3,3,3-trifluoropropyl)succinate With palladium diacetate In diethyl ether; water at 0℃; for 3h; | 81% |
N-Methyl-N'-nitro-N-nitrosoguanidine
diazomethane
Conditions | Yield |
---|---|
With potassium hydroxide at -20.1℃; | 80% |
With potassium hydroxide | |
With potassium hydroxide In diethyl ether; water for 0.25h; |
Conditions | Yield |
---|---|
In methanol; water for 2h; Heating; | 80% |
N-Methyl-N'-nitro-N-nitrosoguanidine
Conditions | Yield |
---|---|
With potassium hydroxide In diethyl ether; ethanol; water for 0.166667h; Inert atmosphere; | 78% |
1. | dnd-hmn:fbr 20 µmol/L | ENMUDM Environmental Mutagenesis. 7 (1985),267. | ||
2. | sce-hmn:hla 300 nmol/L | CRNGDP Carcinogenesis. 5 (1984),593. | ||
3. | ivn-rat TDLo:25 mg/kg (15D preg):ETA,TER | KFIZAO Kyoto-furitsu Ika Daigaku Zasshi. Journal of the Kyoto Prefectural School of Medicine. 84 (1975),23. | ||
4. | orl-rat LD50:90 mg/kg | ZKKOBW Zeitschrift fuer Krebsforschung und Klinische Onkologie. 91 (1978),183. | ||
5. | scu-rat LD50:420 mg/kg | ZEKBAI Zeitschrift fuer Krebsforschung. 69 (1967),103. | ||
6. | ivn-rat LD50:80 mg/kg | EJCAAH European Journal of Cancer. 16 (1980),395. | ||
7. | ipr-mus LD50:66 mg/kg | JJIND8 JNCI, Journal of the National Cancer Institute. 62 (1979),911. | ||
8. | ivn-mus LD50:37,300 µg/kg | NCISP* National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program, Bethesda, MD 20205 JAN86 . | ||
9. | orl-ham LD50:1070 mg/kg | CALEDQ Cancer Letters (Shannon, Ireland). 4 (1978),241. |
Confirmed carcinogen with experimental carcinogenic, tumorigenic, and teratogenic data. Poison by ingestion, intraperitoneal, and intravenous routes. Moderately toxic by subcutaneous route. Experimental reproductive effects. Human mutation data reported. An explosive sensitive to heat or impact. Flammable when exposed to heat or flame; can react vigorously with oxidizing materials. When heated to decomposition it emits very toxic fumes of NOx. See also N-NITROSO COMPOUNDS.
Hazard Codes:T,N,N,T
Risk Statements:
20: Harmful by inhalation
36: Irritating to the eyes
38: Irritating to the skin
45: May cause cancer
51: Toxic to aquatic organisms
53: May cause long-term adverse effects in the aquatic environment
Safety Statements:
45: In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
53: Avoid exposure - obtain special instruction before use
61: Avoid release to the environment. Refer to special instructions safety data sheet
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