Potassium Carbonate → 5-Acetyl-2-aminothieno[3,2-b]thiophene-3-carbonitrile

HRID 1905459Notes

Reaction equation

HRID 1905459 reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH:10]=O)=[C:5](Cl)[C:6]=1[C:7]#[N:8].C(=O)([O-])[O-].[K+].[K+].[CH2:18]([SH:22])[C:19]([CH3:21])=[O:20]>CN(C)C=O>[C:19]([C:18]1[S:22][C:5]2[C:6]([C:7]#[N:8])=[C:2]([NH2:1])[S:3][C:4]=2[CH:10]=1)(=[O:20])[CH3:21]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5201441-Mercapto-2-propanoneHCID 27376122-Amino-4-chloro-5-formyl-3-thiophenecarbonitrile

Product 1

HCID 140473255-Acetyl-2-aminothieno[3,2-b]thiophene-3-carbonitrileYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 18.7 parts of 2-amino-4-chloro-3-cyano-5-formylthiophene, 13.8 parts of potassium carbonate and 80 parts of N,N-dimethylformamide was introduced first, and 9 parts of acetonylmercaptan were then added. After the exothermic reaction had died down, the mixture was heated at 60° C. for 1 hour and then discharged onto water. The precipitate was filtered off with suction, washed with water and dried. This gave 17.9 parts (81% of theory) of 5-acetyl-2-amino-3-cyanothieno[3,2-b]thiophene.

Workup

  1. additionwas introduced first
  2. customAfter the exothermic reaction
  3. filtrationThe precipitate was filtered off with suction
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-978a397eb93e43c3971ae9a844a69f10
Source dataset
uspto-grants-1989_06
Patent number
US04843153

Reaction notes

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