Dimethylformamide dimethyl acetal → N,N-Dimethyl-N'-(6-hydroxybenzothiazole-2-sulfonyl)formamidine

HRID 2164613Notes

Reaction equation

HRID 2164613 reaction equation
CO[CH:3](OC)[N:4]([CH3:6])[CH3:5].[OH:9][C:10]1[CH:22]=[CH:21][C:13]2[N:14]=[C:15]([S:17]([NH2:20])(=[O:19])=[O:18])[S:16][C:12]=2[CH:11]=1>C(#N)C>[CH3:6][N:4]([CH3:5])[CH:3]=[N:20][S:17]([C:15]1[S:16][C:12]2[CH:11]=[C:10]([OH:9])[CH:22]=[CH:21][C:13]=2[N:14]=1)(=[O:18])=[O:19]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 68521296-Hydroxy-1,3-benzothiazole-2-sulfonamide

Product 1

HCID 54375873N,N-Dimethyl-N'-(6-hydroxybenzothiazole-2-sulfonyl)formamidine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N,N-Dimethylformamide dimethyl acetal (1.5 mL, 11.3 mmol) was added to a partial suspension of 6-hydroxybenzothiazole-2-sulfonamide (2.3 gm, 10 mmol) in acetonitrile (20 mL) to give an immediate solution. After stirring at room temperature for 1 hour, the reaction mixture was cooled and the crystalline product which formed (1.95 gm) was collected m.p. 195°-198° C. Evaporation of the reaction solvent and dissolution of the residue in ethyl acetate/acetonitrile which was washed with water, dried (Na2SO4) and evaporated yielded an additional 0.6 gm from methylene chloride.

Workup

  1. customto give an immediate solution
  2. temperaturethe reaction mixture was cooled
  3. customthe crystalline product which formed (1.95 gm)
  4. customwas collected m.p. 195°-198° C
  5. customEvaporation of the reaction solvent and dissolution of the residue in ethyl acetate/acetonitrile which
  6. washwas washed with water
  7. dry with materialdried (Na2SO4)
  8. customevaporated
  9. customyielded an additional 0.6 gm from methylene chloride

Sources & evidence

ORD record
ord-994f65202ef24baf9fabeca17d9d6211
Source dataset
uspto-grants-1985_03
Patent number
US04505923

Reaction notes

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