Methanethioamide → HCID 3395423, compound

HRID 1030456Notes

Reaction equation

HRID 1030456 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=O)[CH2:16]Br)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:19]([NH2:21])=[S:20]>C(O)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:21]=[CH:19][S:20][CH:16]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 3005587MethanethioamideHCID 105425931-[4-(Benzyloxy)phenyl]-2-bromoethan-1-one

Product 1

HCID 3395423HCID 3395423, compoundYield 27.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4'-benzyloxy-2-bromoacetophenone (3.0 g) and thioformamide (0.63 g) in ethanol (50 ml) was refluxed under heating for 30 minutes. The reaction mixture was poured into ice-water, and the precipitating crystals were collected by filtration, extracted with diethyl ether and purified by column chromatography on silica gel [eluting solvent: methylene chloride-hexane (1:9)] to give 4-(4-benzyloxyphenyl) thiazole (720 mg, 27.7%), which was further purified by recrystallization from diethyl ether-hexane. m.p. 109°-110° C.

Workup

  1. temperaturewas refluxed
  2. temperatureunder heating for 30 minutes
  3. filtrationthe precipitating crystals were collected by filtration
  4. extractionextracted with diethyl ether
  5. custompurified by column chromatography on silica gel [eluting solvent: methylene chloride-hexane (1:9)]

Sources & evidence

ORD record
ord-f69729f762b04d168eed1ce61eafa0ea
Source dataset
uspto-grants-1992_04
Patent number
US05106732

Reaction notes

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