Dimethylformamide → N'-(4-chloro-3-cyano-5-formyl-2-thienyl)-N,N-dimethylformamidine

HRID 1111523Notes

Reaction equation

HRID 1111523 reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH:10]=[O:11])=[C:5]([Cl:9])[C:6]=1[C:7]#[N:8].ClCC(O)=C(C#N)C#N.C(#N)CC#N.ClCC(Cl)=O.[NH4+]=S.NC1SC=C(O)C=1C#N.P(Cl)(Cl)(Cl)=O.[CH3:47][N:48]([CH3:51])[CH:49]=O>C(N(CC)CC)C>[Cl:9][C:5]1[C:6]([C:7]#[N:8])=[C:2]([N:1]=[CH:47][N:48]([CH3:51])[CH3:49])[S:3][C:4]=1[CH:10]=[O:11]

Participants

9

Reactant 7

HCID 6228DimethylformamideHCID 6577Chloroacetyl chlorideHCID 8010MalononitrileHCID 24813Phosphorus oxychlorideHCID 27376122-Amino-4-chloro-5-formyl-3-thiophenecarbonitrileHCID 135480882-Amino-4-hydroxythiophene-3-carbonitrileHCID 144385423-Chloro-1,1-dicyano-2-hydroxy-1-propene

Product 1

HCID 54382946N'-(4-chloro-3-cyano-5-formyl-2-thienyl)-N,N-dimethylformamidine

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent2×

Procedure

The preparation of 2-amino-4-chloro-3-cyano-5-formylthiophene is known from EP-A-No. 193 885, according to which the intermediate triethylamine salt of 3-chloro-1,1-dicyano-2-hydroxy-1-propene is prepared from malononitrile, chloroacetyl chloride, and triethylamine and cyclized with ammonium sulfide to 2-amino-3-cyano-4-hydroxythiophene, which is then treated with a mixture of N,N-dimethylformamide and phosphoryl chloride; the N'-(4-chloro-3-cyano-5-formyl-2-thienyl)-N,N-dimethylformamidine that is formed is isolated and then hydrolyzed with formic acid, giving the required product. However, it has been found that the yield of 2-amino-4-chloro-3-cyano-5-formylthiophene obtained by this process is unsatisfactory.

Sources & evidence

ORD record
ord-509d363a75d041559625692be15c1511
Source dataset
uspto-grants-1990_12
Patent number
US04980495

Reaction notes

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