Phenacyl bromide → HCID 20558012, compound

HRID 1660156Notes

Reaction equation

HRID 1660156 reaction equation
[C:1]1([CH2:6][NH:7][C:8]([NH2:10])=[S:9])[S:5][CH:4]=[CH:3][CH:2]=1.[Br:11][CH2:12][C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=O>C(O)C>[BrH:11].[C:1]1([CH2:6][NH:7][C:8]2[S:9][CH:12]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:10]=2)[S:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 6259Phenacyl bromideHCID 5374306HCID 5374306, compound

Product 1

HCID 20558012HCID 20558012, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-thenylthiourea (2.0 grams, 0.0116 moles) and α-bromoacetophenone (2.3 grams, 0.0116 moles, Aldrich Chem. Co.) in 15 ml absolute ethanol were heated to reflux temperature for 90 minutes under nitrogen. The reaction mixture was cooled and the ethanol removed under vacuum. On dissolving the residue in hot isopropyl alcohol and diluting with diethyl ether, an oil was formed. The diethyl ether was decanted, the oil dissolved in a small amount of ethanol and cooled. The resulting solids were filtered and dried over phosphorus pentoxide, yielding 3.20 grams (78%) of 2-thenylamino-4-phenyl-thiazole hydrobromide, m.p. 115°-118° C.

Workup

  1. temperatureto reflux temperature for 90 minutes under nitrogen
  2. temperatureThe reaction mixture was cooled
  3. customthe ethanol removed under vacuum
  4. dissolutionOn dissolving the residue in hot isopropyl alcohol
  5. additiondiluting with diethyl ether
  6. customan oil was formed
  7. customThe diethyl ether was decanted
  8. dissolutionthe oil dissolved in a small amount of ethanol
  9. temperaturecooled
  10. filtrationThe resulting solids were filtered
  11. dry with materialdried over phosphorus pentoxide

Sources & evidence

ORD record
ord-631faf652a2b4e2eaaee5b1478043562
Source dataset
uspto-grants-1981_12
Patent number
US04307106

Reaction notes

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