Ethanol → HCID 54280119, compound

HRID 728992Notes

Reaction equation

HRID 728992 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH2:9])=[S:8])=[CH:5][CH:4]=1.C(O)C.Cl[CH:16]([CH3:20])[C:17](=O)[CH3:18]>CCOCC>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]2[S:8][C:16]([CH3:20])=[C:17]([CH3:18])[N:9]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 200263-Chloro-2-butanone2×HCID 7368274-Methoxybenzenecarbothioamide

Product 1

HCID 54280119HCID 54280119, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred mixture of 65.1 g (4-methoxy)thiobenzamide and 156 ml ethanol was added dropwise 50.1 g 3-chloro-2-butanone, and the reaction mixture was heated at reflux for 3 hours. An additional 6.1 g 2-chloro-3-butanone was added and heating was continued for an additional hour. The reaction mixture was cooled, 300 ml ether added, and the solid which precipitated was collected and dried to give 74.5 g 2-(4-methoxyphenyl)-4,5-dimethylthiazole in the form of its hydrochloride monohydrate, m.p. 166°-170° C.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 3 hours
  3. temperatureheating
  4. waitwas continued for an additional hour
  5. temperatureThe reaction mixture was cooled
  6. customthe solid which precipitated
  7. customwas collected
  8. customdried

Sources & evidence

ORD record
ord-b508029375244457a2b8b79ffa047bd7
Source dataset
uspto-grants-1991_09
Patent number
US05051437

Reaction notes

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