Hydrochloric Acid → (2E)-3-(2-anilinothiazol-4-yl)acrylaldehyde

HRID 2107267Notes

Reaction equation

HRID 2107267 reaction equation
[NH:1]([C:8]1[S:9][CH:10]=[C:11]([CH:13]=[CH:14][CH2:15][OH:16])[N:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.O.Cl>CS(C)=O>[NH:1]([C:8]1[S:9][CH:10]=[C:11](/[CH:13]=[CH:14]/[CH:15]=[O:16])[N:12]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8471TriethylamineHCID 538556963-(2-Anilinothiazol-4-yl)allyl alcohol

Product 1

HCID 15053531(2E)-3-(2-anilinothiazol-4-yl)acrylaldehyde

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

2.6 g of the crude alcohol thus obtained were dissolved in 20 ml of dimethyl sulfoxide, and 3.4 g of triethylamine were added to the resulting solution. Next, a solution of 5.3 g of a sulfur trioxide pyridine complex in dimethyl sulfoxide (10 ml) was added dropwise to the reaction mixture at room temperature, and the mixture was stirred at the same temperature for 30 minutes. The reaction mixture was then poured into water, acidified with 3N hydrochloric acid, and extracted with ethyl acetate. After the extract was dried over anhydrous sodium sulfate, the solvent was evaporated off under reduced pressure. The residue was purified by silica gel column chromatography, using as eluent a 10:1 mixture of benzene and ethyl acetate, giving the desired compound as pale yellow crystals.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialAfter the extract was dried over anhydrous sodium sulfate
  3. customthe solvent was evaporated off under reduced pressure
  4. customThe residue was purified by silica gel column chromatography
  5. additiona 10:1 mixture of benzene and ethyl acetate

Sources & evidence

ORD record
ord-145429a92b7049ba9c4bcbb743566ee3
Source dataset
uspto-grants-1990_06
Patent number
US04933355

Reaction notes

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