Dimethyl Sulfoxide → 2-Anilinothiazole-4-carbaldehyde

HRID 2107261Notes

Reaction equation

HRID 2107261 reaction equation
CS(C)=O.[NH:5]([C:12]1[S:13][CH:14]=[C:15]([CH2:17][OH:18])[N:16]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(N(CC)CC)C>O>[NH:5]([C:12]1[S:13][CH:14]=[C:15]([CH:17]=[O:18])[N:16]=1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 679Dimethyl Sulfoxide2×HCID 8471TriethylamineHCID 15053553HCID 15053553, compound

Product 1

HCID 150535702-Anilinothiazole-4-carbaldehyde

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A dimethyl sulfoxide solution (120 ml) of 20 g of sulfur trioxide pyridine complex was added dropwise to a mixture comprising 8.3 g of 2-anilinothiazol-4-ylmethanol, 16.5 ml of triethylamine and 120 ml of dimethyl sulfoxide. The resulting mixture was stirred at room temperature for 10 minutes and then poured into water. followed by extraction with ethyl acetate. The extract was washed successively with aqueous acetic acid, aqueous sodium chloride solution and aqueous sodium hydrogen carbonate solution, and dried over anhydrous sodium sulfate. The residue afforded by evaporation of the solvent under reduced pressure was recrystallized from a mixture of benzene and acetone. The resulting product was a brown powder having the following physical properties.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe extract was washed successively with aqueous acetic acid, aqueous sodium chloride solution and aqueous sodium hydrogen carbonate solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe residue afforded by evaporation of the solvent under reduced pressure
  5. customwas recrystallized from a mixture of benzene and acetone

Sources & evidence

ORD record
ord-cec89db97521440fba29f14be0d6d555
Source dataset
uspto-grants-1990_06
Patent number
US04933355

Reaction notes

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