Acetic Anhydride → 2-(2-(3-Cyanophenyl)ethenyl)-4-isopropylthiazole

HRID 1650681Notes

Reaction equation

HRID 1650681 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=O)#[N:2].[CH:11]([C:14]1[N:15]=[C:16]([CH3:19])[S:17][CH:18]=1)([CH3:13])[CH3:12].C(OC(=O)C)(=O)C>C(O)(=O)C>[C:1]([C:3]1[CH:4]=[C:5]([CH:6]=[CH:19][C:16]2[S:17][CH:18]=[C:14]([CH:11]([CH3:13])[CH3:12])[N:15]=2)[CH:8]=[CH:9][CH:10]=1)#[N:2]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 90670m-FormylbenzonitrileHCID 5205692-Methyl-4-(1-methylethyl)thiazole

Product 1

HCID 537541442-(2-(3-Cyanophenyl)ethenyl)-4-isopropylthiazoleYield 54%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
170 °C

Procedure

3-Cyanobenzaldehyde (3.93 g, 30.0 mmol) was mixed with 4-isopropyl-2-methylthiazole (4.19 g, 30.0 mmol), and acetic anhydride (1.53 g, 15.0 mmol) was added. The mixture was heated under stirring at 170° C for 24 hours. After the reaction, acetic acid was distilled out under reduced pressure and the residue was purified by column chromatography (SiO2, n-hexane/ethyl acetate=3/l) to afford the indicated compound (4.10 g) with a yield of 54%.

Workup

  1. additionwas added
  2. temperatureThe mixture was heated
  3. distillationwas distilled out under reduced pressure
  4. customthe residue was purified by column chromatography (SiO2, n-hexane/ethyl acetate=3/l)

Sources & evidence

ORD record
ord-f125d88b10834ed9bfd2759a97c0e60b
Source dataset
uspto-grants-1990_05
Patent number
US04925861

Reaction notes

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