Methanethioamide → HCID 13015600, compound

HRID 1058348

Reaction equation

HRID 1058348 reaction equation
[CH:1]([NH2:3])=[S:2].[CH2:4]([O:6][C:7](=[O:15])[CH:8](Cl)[C:9](=O)[CH:10]([CH3:12])[CH3:11])[CH3:5]>C(O)C>[CH2:4]([O:6][C:7]([C:8]1[S:2][CH:1]=[N:3][C:9]=1[CH:10]([CH3:12])[CH3:11])=[O:15])[CH3:5]

Participants

4

Reactant 2

HCID 3005587MethanethioamideHCID 9877606Ethyl 2-chloro-4-methyl-3-oxopentanoate

Product 1

HCID 13015600HCID 13015600, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of thioformamide (prepared according to A1-Razzar et al. U.S. Pat, No. 5,559158; 1.2 g, 20 mmol) and 2-chloro-4-methyl-3-oxopentanoic acid ethyl ester (2.0 g, 10 mmol) in ethanol (20 mL) was heated at reflux for 17 h. The reaction mixture was evaporated to dryness and the residue was chromatographed over silica gel (5-20% ethyl acetate/hexanes) to give 4-(1-methylethyl)thiazole-5-carboxylic acid ethyl ester (720 mg, 36% yield).

Workup

  1. temperatureat reflux for 17 h
  2. customThe reaction mixture was evaporated to dryness
  3. customthe residue was chromatographed over silica gel (5-20% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-129a30faf3f14682a1471b9b795211e5
Source dataset
uspto-grants-2003_02
Patent number
US06515124B2

Linked notes

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