Acetic Anhydride → 2-(5-Methyl-4-phenyl-2-thioxothiazol-3-yl)ethyl Acetate

HRID 2122000Notes

Reaction equation

HRID 2122000 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[C:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:7]([CH3:15])[S:6][C:5]1=[S:16].[C:17](OC(=O)C)(=[O:19])[CH3:18]>C(Cl)(Cl)Cl>[C:17]([O:1][CH2:2][CH2:3][N:4]1[C:8]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[C:7]([CH3:15])[S:6][C:5]1=[S:16])(=[O:19])[CH3:18]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 219374123-(2-hydroxyethyl)-5-methyl-4-phenyl-3H-thiazole-2-thione

Product 1

HCID 219375452-(5-Methyl-4-phenyl-2-thioxothiazol-3-yl)ethyl Acetate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Intermediate 3-(2-hydroxyethyl)-5-methyl-4-phenyl-3H-thiazole-2-thione was treated with acetic anhydride (1 equiv) and TEA (2 equiv) in CHCl3. After 12 h the product mixture was concentrated and chromatographed (silica gel, 0-40% EtOAc/Hex) to afford the title compound. 1H-NMR (CDCl3): δ 7.50-7.55 (3H, m), 7.28-7.32 (2H, m), 4.32 (2H, t), 4.26 (2H, t), 2.03 (3H, s), 1.93 (3H, s).

Workup

  1. concentrationAfter 12 h the product mixture was concentrated
  2. customchromatographed (silica gel, 0-40% EtOAc/Hex)

Sources & evidence

ORD record
ord-95961a1562d544acaf2a3258ce96c5c3
Source dataset
uspto-grants-2004_02
Patent number
US06696473B2

Reaction notes

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