Hydrochloric Acid → HCID 13215562, compound

HRID 2232383Notes

Reaction equation

HRID 2232383 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([NH2:10])=[S:9])=[CH:4][CH:3]=1.CO[CH:13](OC)[CH2:14]Br.Cl>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][CH:13]=[CH:14][N:10]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 816722-Bromo-1,1-dimethoxyethaneHCID 27348264-Chlorothiobenzamide

Product 1

HCID 13215562HCID 13215562, compoundYield 34.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred mixture of 12.1 grams (0.0703 mole) of 4-chlorophenylthiocarboxamide, 12.1 grams (0.0714 mole) of bromoacetaldehyde dimethyl acetal, and 2 ml of concentrated hydrochloric acid in 280 ml of ethanol was heated at reflux for approximately 18 hours. An additional 1 ml of concentrated hydrochloric acid was added, and the mixture was heated at reflux for two days. The reaction mixture was cooled, and the solvent was removed by evaporation under reduced pressure leaving a residue. This residue was purified by column chromatography on silica gel, eluting with methylene chloride:n-hexane (3:1), to yield 4.8 grams of 2-(4-chlorophenyl)thiazole as a solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for approximately 18 hours
  3. temperaturethe mixture was heated
  4. temperatureat reflux for two days
  5. temperatureThe reaction mixture was cooled
  6. customthe solvent was removed by evaporation under reduced pressure
  7. customleaving a residue
  8. customThis residue was purified by column chromatography on silica gel
  9. washeluting with methylene chloride:n-hexane (3:1)

Sources & evidence

ORD record
ord-3949ba103d99450490a3928abea93655
Source dataset
uspto-grants-1988_11
Patent number
US04788207

Reaction notes

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