Chloroacetyl chloride → 2-Amino-4-hydroxythiophene-3-carbonitrile

HRID 1591283Notes

Reaction equation

HRID 1591283 reaction equation
C(N(CC)CC)C.Cl[CH2:9][C:10](Cl)=[O:11].[CH2:13]([C:16]#[N:17])[C:14]#[N:15].[NH4+]=[S:19]>O.CN(C)C=O>[NH2:15][C:14]1[S:19][CH:9]=[C:10]([OH:11])[C:13]=1[C:16]#[N:17]

Participants

6

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8010MalononitrileHCID 8471Triethylamine

Product 1

HCID 135480882-Amino-4-hydroxythiophene-3-carbonitrileYield 62%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

350 parts of triethylamine are added dropwise to a mixture of 178 parts of chloroacetyl chloride, 104 parts of malonodinitrile and 900 parts of dimethylformamide, while cooling with ice. The solution is stirred for a further hour at room temperature, after which it is introduced into a mixture of 294.5 parts of a 40% strength aqueous ammonium sulfide solution, 1000 parts of ice and 1000 parts of water, and the reaction mixture is stirred for a further 3 hours at room temperature. The precipitate formed is filtered off under suction, washed with water and dried. 137 parts (62% of theory) of 2-amino-3-cyano-4-hydroxythiophene are obtained.

Workup

  1. temperaturewhile cooling with ice
  2. stirringthe reaction mixture is stirred for a further 3 hours at room temperature
  3. customThe precipitate formed
  4. filtrationis filtered off under suction
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-345e9a372a994b808c471b5a24ccbcdd
Source dataset
uspto-grants-1993_04
Patent number
US05206375

Reaction notes

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