Acetic Acid → 3-(2-(4-(1-Methylethyl)-2-thiazolyl)ethenyl)benzaldehyde

HRID 1088486Notes

Reaction equation

HRID 1088486 reaction equation
[CH3:1][CH:2]([C:4]1[N:5]=[C:6]([CH3:9])[S:7][CH:8]=1)[CH3:3].C(O[C:14](=[O:16])[CH3:15])(=O)C.C(O)(=O)C.[C:21]1([CH3:27])[CH:26]=C[CH:24]=[CH:23][CH:22]=1>>[CH3:1][CH:2]([C:4]1[N:5]=[C:6]([CH:9]=[CH:27][C:21]2[CH:26]=[C:15]([CH:24]=[CH:23][CH:22]=2)[CH:14]=[O:16])[S:7][CH:8]=1)[CH3:3]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 1140TolueneHCID 7918Acetic AnhydrideHCID 5205692-Methyl-4-(1-methylethyl)thiazole

Product 1

HCID 540138533-(2-(4-(1-Methylethyl)-2-thiazolyl)ethenyl)benzaldehyde

Procedure

4-(1-Methylethyl)-2-methylthiazole (546 mg, EP 0219436 p. 19) and isophthaladehyde (570 mg, 1.1 equiv.) are heated at reflux in acetic anhydride (1.1 mL, 3 equiv.) 16 hours. The reaction mixture is cooled and the acetic acid and anhydride are co-evaporated with toluene. The title compound is purified by flash chromatography on silica using EtOAc:hexane 10:90.

Workup

  1. temperatureThe reaction mixture is cooled
  2. customThe title compound is purified by flash chromatography on silica

Sources & evidence

ORD record
ord-c88d99a0ca7245358ebb6512e838011e
Source dataset
uspto-grants-1990_10
Patent number
US04962117

Reaction notes

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