Phenacyl bromide → 2-Amino-4-phenylthiazole

HRID 1971495Notes

Reaction equation

HRID 1971495 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=O.[NH2:11][C:12]([NH2:14])=[S:13]>CO>[C:5]1([C:3]2[N:11]=[C:12]([NH2:14])[S:13][CH:2]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 6259Phenacyl bromideHCID 2723790Thiourea

Product 1

HCID 403022-Amino-4-phenylthiazoleYield 95.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Bromo-1-phenyl-ethanone (19.9 g, 0.100 mol) and thiourea (7.9 g, 0.10 mol) were mixed in a 150 mL of methanol. The reaction mixture was warmed to dissolve the reagents and then allowed to stir overnight at room temperature. The methanol was evaporated to dryness and the crude product was dissolved in a minimum of ethyl acetate. The crude product was then extracted twice with 1M sodium hydroxide and once with a saturated aqueous solution of sodium chloride. The organic layer was then dried over sodium sulfate, filtered, and evaporated to dryness to yield the pure product (16.8 g, 0.0953 mol, 95.3%) of product. ESI-MS m/z calc. 176.0. found 177.2 (M+1)+ Retention time 1.41 minutes. 1H NMR (400 MHz, CD3CN) δ 5.73 (s, 2H), 6.87 (s, 1H), 7.28-7.34 (m, 1H), 7.36-7.43 (m, 2H), 7.79-7.85 (m, 2H).

Workup

  1. temperatureThe reaction mixture was warmed
  2. dissolutionto dissolve the reagents
  3. customThe methanol was evaporated to dryness
  4. dissolutionthe crude product was dissolved in a minimum of ethyl acetate
  5. extractionThe crude product was then extracted twice with 1M sodium hydroxide and once with a saturated aqueous solution of sodium chloride
  6. dry with materialThe organic layer was then dried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-ecccac418a804ee2a1fc1a62c984fb74
Source dataset
uspto-grants-2013_04
Patent number
US08431605B2

Reaction notes

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