Dimethylformamide dimethyl acetal → N,N-Dimethyl-N'-(thieno[2,3-c]pyridine-2-sulfonyl)formamidine

HRID 569052Notes

Reaction equation

HRID 569052 reaction equation
[S:1]([C:5]1[S:13][C:8]2=[CH:9][N:10]=[CH:11][CH:12]=[C:7]2[CH:6]=1)(=[O:4])(=[O:3])[NH2:2].CO[CH:16](OC)[N:17]([CH3:19])[CH3:18]>C(#N)C.C(Cl)(Cl)Cl>[CH3:16][N:17]([CH3:19])[CH:18]=[N:2][S:1]([C:5]1[S:13][C:8]2=[CH:9][N:10]=[CH:11][CH:12]=[C:7]2[CH:6]=1)(=[O:3])=[O:4]

Participants

5

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 20148577Thieno[2,3-c]pyridine-2-sulfonamide

Product 1

HCID 54324967N,N-Dimethyl-N'-(thieno[2,3-c]pyridine-2-sulfonyl)formamidineYield 96.1%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6342AcetonitrileSolvent

Procedure

To a partial suspension of 2-sulfamoylthieno[2,3-c]pyridine (1.81 g, 8.5 mmol) in acetonitrile (20 ml), under a nitrogen atmosphere, was added dropwise dimethylformamide dimethyl acetal (1.3 ml, 9.7 mmol). After 2 hours, the mixture was diluted with chloroform, washed with water, dried over anhydrous sodium sulfate, filtered and evaporated to give 2.2 g of product. This material was recrystallized from ethyl acetate to give 2.05 g (90% yield); m.p. 169°-171° C. Analysis calculated for C10H11N3O2S2 : N, 15.60; C, 44.59, H, 4.12. Found: N, 15.79; C, 44.95; H, 4.08.

Workup

  1. washwashed with water
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-7ebb426ab8574a62bdd75d012c21e9cd
Source dataset
uspto-grants-1988_03
Patent number
US04731368

Reaction notes

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