Hydrochloric Acid → N,N-dimethyl-N'-(3-cyano-5-ethoxycarbonylthieno[3,2-b]thien-2-yl)formamidine

HRID 1905460Notes

Reaction equation

HRID 1905460 reaction equation
[C:1]([O:5][CH2:6][CH3:7])(=[O:4])[CH2:2][SH:3].[CH3:8][N:9]([CH3:22])[CH:10]=[N:11][C:12]1[S:13][C:14]([CH:20]=O)=[C:15](Cl)[C:16]=1[C:17]#[N:18].C(=O)([O-])[O-].[K+].[K+].Cl>O.CN(C)C=O>[CH3:22][N:9]([CH3:8])[CH:10]=[N:11][C:12]1[S:13][C:14]2[CH:20]=[C:2]([C:1]([O:5][CH2:6][CH3:7])=[O:4])[S:3][C:15]=2[C:16]=1[C:17]#[N:18]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 12185Ethyl ThioglycolateHCID 54382946N'-(4-chloro-3-cyano-5-formyl-2-thienyl)-N,N-dimethylformamidine

Product 1

HCID 68115437N,N-dimethyl-N'-(3-cyano-5-ethoxycarbonylthieno[3,2-b]thien-2-yl)formamidineYield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

120 parts of ethyl thioglycolate were added to a mixture of 241.5 parts of N,N-dimethyl-N'-(4-chloro-3-cyano-5-formylthien-2-yl)formamidine, 138 parts of potassium carbonate and 1,400 parts of N,N-dimethylformamide. After the slightly exothermic reaction had died down, the reaction mixture was stirred at 50° C. for 2 hours. 1,000 parts of ice, 1,000 parts of water and 150 parts of concentrated hydrochloric acid were then added. The precipitate was filtered off with suction, washed with water and dried. This gave 284 parts (93% of theory) of N,N-dimethyl-N'-(3-cyano-5-ethoxycarbonylthieno[3,2-b]thien-2-yl)formamidine.

Workup

  1. customAfter the slightly exothermic reaction
  2. filtrationThe precipitate was filtered off with suction
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-d56900313ebd4ca9ab8198c03269c71f
Source dataset
uspto-grants-1989_06
Patent number
US04843153

Reaction notes

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