Ethyl formate → Cyanoacetamide

HRID 866982

Reaction equation

HRID 866982 reaction equation
[Na].[CH3:2][N:3]([CH3:18])S(C1C=CC(C(CC=O)=O)=CC=1)(=O)=O.C[O-].[Na+].C([O:24][CH2:25][CH3:26])=O.C(C1C=CC(S([N:39]([CH3:41])C)(=O)=O)=CC=1)(=O)C.[O:42]1[CH2:46][CH2:45][CH2:44][CH2:43]1>O>[C:18]([CH2:26][C:25]([NH2:39])=[O:24])#[N:3].[O:42]=[C:46]1[NH:39][CH:41]=[CH:43][CH:44]=[C:45]1[C:2]#[N:3]

Participants

9

Reactant 6

HCID 8025Ethyl formateHCID 8028Tetrahydrofuran2×HCID 20640414-acetyl-N,N-dimethylbenzene-1-sulfonamideHCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 54574074HCID 54574074, compound

Product 2

HCID 7898CyanoacetamideHCID 5775433-Cyano-2-pyridone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

From a solution of the sodium salt of 4-(dimethylaminosulfonyl)benzoylacetaldehyde in 2 l. of water (prepared from 36.1 g. of sodium methoxide in 500 ml. of tetrahydrofuran, 49.5 g. of ethyl formate, and a solution of 137.8 g. of 4-acetyl-N,N-dimethylbenzenesulfonamide in 1.4 l. of tetrahydrofuran) and 76.6 g. of cyanoacetamide, there is obtained 6-[4-dimethylaminosulfonyl)phenyl]-1,2-dihydro-2-oxonicotinonitrile; m.p. 263°-267° C. (dec.) after crystallization from aqueous dimethylformamide.

Sources & evidence

ORD record
ord-77f505c5350d46dcbfd9a1c8963a1163
Source dataset
uspto-grants-1978_07
Patent number
US04101661

Linked notes

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