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inquiryN,N-dimethyl-formamide dimethyl acetal
cyanoacetic acid
3-dimethylaminoacrylonitrile
Conditions | Yield |
---|---|
In 1,4-dioxane at 80℃; for 2h; | 100% |
In 1,4-dioxane at 20 - 90℃; for 16h; |
(methoxymethylidene)dimethylammonium methyl sulfate
sodium cyanoacetate
3-dimethylaminoacrylonitrile
Conditions | Yield |
---|---|
In ethanol at 30℃; for 10h; Temperature; Solvent; | 97.4% |
Conditions | Yield |
---|---|
In water at 20℃; for 20h; | 94% |
2-dimethylamino-2-ethoxy-1-cyanoethylene
3-dimethylaminoacrylonitrile
Conditions | Yield |
---|---|
With platinum on carbon; hydrogen In ethanol at 50℃; under 30003 Torr; for 16h; Autoclave; | 65% |
With platinum on carbon; hydrogen |
Conditions | Yield |
---|---|
In benzene 80 deg C, then 105 deg C, 2 h; | A n/a B 8% |
In benzene 80 deg C, then 105 deg C, 2 h; Title compound not separated from byproducts; |
Conditions | Yield |
---|---|
Conditions | Yield |
---|---|
for 120h; Heating; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
MeCN*HCl
N,N-dimethyl-formamide dimethyl acetal
3-dimethylaminoacrylonitrile
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 110℃; for 9h; |
(methoxymethylidene)dimethylammonium methyl sulfate
cyanoacetic acid
3-dimethylaminoacrylonitrile
Conditions | Yield |
---|---|
Stage #1: (methoxymethylidene)dimethylammonium methyl sulfate; cyanoacetic acid In ethanol at 5 - 40℃; Stage #2: With sodium hydroxide In water-d2 pH=8; Stage #3: In toluene at 5 - 50℃; Temperature; pH-value; Irradiation; |
Conditions | Yield |
---|---|
at 120℃; under 225.023 Torr; Temperature; Pressure; Cooling with ice; |
trifluoracetyl chloride
3-dimethylaminoacrylonitrile
2-((dimethylamino)methylene)-4,4,4-trifluoro-3-oxobutyronitrile
Conditions | Yield |
---|---|
With pyridine In toluene Product distribution / selectivity; Cooling with ice; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In ethyl acetate at 20℃; | 97% |
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In ethyl acetate at 20℃; | 96% |
3-dimethylaminoacrylonitrile
(S)-tert-butyl 2-(chloro(hydroxyimino)methyl)pyrrolidine-1-carboxylate
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In ethyl acetate at 20℃; | 95% |
3-dimethylaminoacrylonitrile
methyl 5-acetamido-2-amino-4-ethoxybenzoate
methyl 5-acetamido-2-[(2-cyanovinyl)amino]-4-ethoxybenzoate
Conditions | Yield |
---|---|
Stage #1: methyl 5-acetamido-2-amino-4-ethoxybenzoate; acetic acid at 20℃; Stage #2: 3-dimethylaminoacrylonitrile at 25 - 30℃; Product distribution / selectivity; | 94.8% |
With acetic acid at 20℃; for 5h; Large scale; | 92% |
3-dimethylaminoacrylonitrile
trifluoroacetic acid
2-((dimethylamino)methylene)-4,4,4-trifluoro-3-oxobutyronitrile
Conditions | Yield |
---|---|
With phosgene; triethylamine In toluene at 5 - 25℃; Product distribution / selectivity; | 94% |
With triethylamine In toluene at 5℃; for 3h; | 92.12% |
With oxalyl dichloride; triethylamine; N,N-dimethyl-formamide In toluene at 20℃; Product distribution / selectivity; Cooling with ice; | 89% |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In dichloromethane at 28℃; for 4h; Solvent; Reagent/catalyst; | 94% |
With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 4h; Temperature; Reagent/catalyst; Friedel-Crafts Alkylation; | 93% |
3-dimethylaminoacrylonitrile
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In ethyl acetate at 20℃; | 94% |
tert-butyl (2R)-2-[chloro(hydroxyimino)methyl]pyrrolidine-1-carboxylate
3-dimethylaminoacrylonitrile
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In ethyl acetate at 20℃; | 93% |
3-dimethylaminoacrylonitrile
acetic acid
(E/Z)-2-((dimethylamino)methylene)-3-oxobutanenitrile
Conditions | Yield |
---|---|
With phosgene; triethylamine In water; toluene at 0 - 20℃; for 3h; | 93% |
3-dimethylaminoacrylonitrile
tert-butyl 4-(chloro(hydroxyimino)methyl)piperidine-1-carboxylate
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In ethyl acetate at 20℃; | 92% |
3-dimethylaminoacrylonitrile
ethyl 5-acetamido-2-amino-4-ethoxybenzoate
ethyl 2-[(2-cyanovinyl)amino]-4-ethoxy-5-acetylamidobenzoate
Conditions | Yield |
---|---|
In 1,2-dimethoxyethane at 20℃; for 12h; | 89% |
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In ethyl acetate at 20℃; | 89% |
pentafluoropropionic acid
3-dimethylaminoacrylonitrile
3-dimethylamino-2-(pentafluoroethylcarbonyl)acrylonitrile
Conditions | Yield |
---|---|
With phosgene; triethylamine In toluene at 5 - 20℃; Cooling with ice; Inert atmosphere; | 88% |
With phosgene; triethylamine In toluene at 5 - 20℃; Inert atmosphere; Cooling with ice; | 88% |
Conditions | Yield |
---|---|
With ammonium cerium (IV) nitrate; thioacetamide In dimethyl sulfoxide at 110℃; for 12h; | 88% |
heptafluorobutyric Acid
3-dimethylaminoacrylonitrile
3-dimethylamino-2-(heptafluoropropylcarbonyl)acrylonitrile
Conditions | Yield |
---|---|
With phosgene; triethylamine In toluene at 6 - 20℃; Inert atmosphere; Cooling with ice; | 86% |
With phosgene; triethylamine In toluene at 6 - 20℃; Cooling with ice; Inert atmosphere; |
(Z)-2-(ethoxymethylene)-4,4-difluoro-3-oxobutanoic acid ethyl ester
3-dimethylaminoacrylonitrile
ethyl 5-cyano-2-(difluoromethyl)nicotinate
Conditions | Yield |
---|---|
Stage #1: (Z)-2-(ethoxymethylene)-4,4-difluoro-3-oxobutanoic acid ethyl ester; 3-dimethylaminoacrylonitrile In N,N-dimethyl-formamide at 60 - 65℃; for 5h; Industry scale; Stage #2: With ammonium acetate In N,N-dimethyl-formamide at 60 - 65℃; for 12h; Industry scale; | 85% |
3-dimethylaminoacrylonitrile
N,N-dimethyl-formamide
ethyl 5-cyano-2-(difluoromethyl)nicotinate
Conditions | Yield |
---|---|
Stage #1: (E/Z)-ethyl 2-(ethoxymethylene)-4,4-difluoro-3-oxobutanoate; 3-dimethylaminoacrylonitrile; N,N-dimethyl-formamide at 60 - 65℃; for 5h; Large scale; Stage #2: With ammonium acetate at 60 - 65℃; for 12h; Large scale; | 85% |
3-dimethylaminoacrylonitrile
2-amino-4-bromo-benzoic acid methyl ester
Conditions | Yield |
---|---|
In ethyl acetate at 20℃; | 85% |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In dichloromethane at 28℃; for 6h; Time; Temperature; Solvent; Reagent/catalyst; | 85% |
difluoroacetyl chloride
3-dimethylaminoacrylonitrile
2-((dimethylamino)methylene)-4,4-difluoro-3-carbonylbutyronitrile
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; for 5h; Solvent; Inert atmosphere; | 84.6% |
3-dimethylaminoacrylonitrile
2-chloro-2,2-difluoroacetic acid
3-dimethylamino-2-(chlorodifluoromethylcarbonyl)acrylonitrile
Conditions | Yield |
---|---|
With phosgene; triethylamine In toluene at 5 - 20℃; Cooling with ice; Inert atmosphere; | 83% |
With phosgene; triethylamine In toluene at 5 - 20℃; Inert atmosphere; Cooling with ice; | 83% |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In dichloromethane at 28℃; for 4h; Reagent/catalyst; | 83% |
1-ethyl-2-phenyl-1H-indole
3-dimethylaminoacrylonitrile
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In dichloromethane at 28℃; for 4h; | A 15% B 83% |
5-fluoro-1-methyl-1H-indole
3-dimethylaminoacrylonitrile
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In dichloromethane at 28℃; for 4h; | 82% |
Conditions | Yield |
---|---|
With dichloro-acetic acid In 1,2-dichloro-ethane at 50℃; for 4h; | 82% |
With dichloro-acetic acid at 50℃; for 4h; Temperature; Time; | 82% |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In dichloromethane at 28℃; for 4h; Reagent/catalyst; Time; | 82% |
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