2-Chloro-4'-fluoroacetophenone → HCID 20558010, compound

HRID 1660157Notes

Reaction equation

HRID 1660157 reaction equation
[C:1]1([CH2:6][NH:7][C:8]([NH2:10])=[S:9])[S:5][CH:4]=[CH:3][CH:2]=1.[Cl:11][CH2:12][C:13]([C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1)=O>C(O)C>[ClH:11].[C:1]1([CH2:6][NH:7][C:8]2[S:9][CH:12]=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)[N:10]=2)[S:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 1202482-Chloro-4'-fluoroacetophenoneHCID 5374306HCID 5374306, compound

Product 1

HCID 20558010HCID 20558010, compoundYield 56.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-thenylthiourea (0.80 grams, 0.0046 moles) and α-chloro-p-fluoroacetophenone (0.80 grams, 0.0046 moles, Aldrich Chem. Co.) in 11 ml absolute ethanol were heated at reflux temperature under nitrogen for 90 minutes. After cooling, and ethanol was removed under vacuum and the solids triturated with ethanol, filtered and vacuum dried over phosphorous pentoxide, yielding 0.848 grams (56%) of 2-thenylamino-4(p-fluorophenyl)-thiazole hydrochloride, m.p. 184°-187° C.

Workup

  1. temperatureat reflux temperature under nitrogen for 90 minutes
  2. temperatureAfter cooling
  3. customethanol was removed under vacuum
  4. customthe solids triturated with ethanol
  5. filtrationfiltered
  6. dry with materialvacuum dried over phosphorous pentoxide

Sources & evidence

ORD record
ord-772cb3f62d884ea9a0aa4fe3a43bfc64
Source dataset
uspto-grants-1981_12
Patent number
US04307106

Reaction notes

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