Acetic Anhydride → N,N-Dimethyl-N'-(7-acetoxythieno[2,3-c]pyridine-2-sulfonyl)formamidine

HRID 569054Notes

Reaction equation

HRID 569054 reaction equation
[CH3:1][N:2]([CH3:18])[CH:3]=[N:4][S:5]([C:8]1[S:17][C:11]2=[CH:12][N+:13]([O-])=[CH:14][CH:15]=[C:10]2[CH:9]=1)(=[O:7])=[O:6].[C:19]([O:22]C(=O)C)(=[O:21])[CH3:20]>>[CH3:1][N:2]([CH3:18])[CH:3]=[N:4][S:5]([C:8]1[S:17][C:11]2=[C:12]([O:22][C:19](=[O:21])[CH3:20])[N:13]=[CH:14][CH:15]=[C:10]2[CH:9]=1)(=[O:7])=[O:6]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 54087375N,N-dimethyl-N'-(6-oxido-thieno[2,3-c]pyridine-2-sulfonyl)formamidine

Product 1

HCID 53999326N,N-Dimethyl-N'-(7-acetoxythieno[2,3-c]pyridine-2-sulfonyl)formamidineYield 50%

Conditions

Temperature
120 °C

Procedure

A mixture of N,N-dimethyl-N'-(6-oxido-thieno[2,3-c]pyridine-2-sulfonyl)formamidine (3.5 g, 12.3 mmol) in acetic anhydride (20 ml), under a nitrogen atmosphere, was heated at 120° C. for 3 hours. The dark solution was poured into ice/water and stirred for 1/2 hour. The product was extracted into methylene chloride, washed with sodium carbonate solution, dried over anhydrous sodium sulfate and evaporated to give 4.77 g of crude product. This residue was triturated with methylene chloride/diethyl ether to give 2.0 g (50% yield) of pure product. Recrystallization from ethyl acetate gave product with a broad melting point of 184°-191° C.

Workup

  1. extractionThe product was extracted into methylene chloride
  2. washwashed with sodium carbonate solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated
  5. customto give 4.77 g of crude product
  6. customThis residue was triturated with methylene chloride/diethyl ether

Sources & evidence

ORD record
ord-45a3da72f2c04f8e936f060c49a63051
Source dataset
uspto-grants-1988_03
Patent number
US04731368

Reaction notes

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