Bromomethyl 3-methoxyphenyl ketone → 4-(3-methoxyphenyl)-1,3-thiazol-2-amine

HRID 533963Notes

Reaction equation

HRID 533963 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[CH:6]=1)=O.[NH2:13][C:14]([NH2:16])=[S:15]>C(O)C>[CH3:12][O:11][C:7]1[CH:6]=[C:5]([C:3]2[N:13]=[C:14]([NH2:16])[S:15][CH:2]=2)[CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 101294Bromomethyl 3-methoxyphenyl ketoneHCID 2723790Thiourea

Product 1

HCID 7346294-(3-methoxyphenyl)-1,3-thiazol-2-amineYield 94.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Bromo-1-(3-methoxy-phenyl)-ethanone (0.7291 g, 3.183 mmol) and thiourea (0.2665 g, 3.501 mmol) were dissolved in a 20 mL of ethanol. The reaction mixture was allowed to stir overnight at room temperature. The ethanol was evaporated to dryness and the crude product was dissolved in a minimum of dichloromethane. 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 product (0.619 g, 3.00 mmol, 94.3%). ESI-MS m/z calc. 206.3. found 207.0 (M+1)+ Retention time 1.86 minutes. 1H NMR (400 MHz, CD3CN) δ 3.84 (s, 3H), 5.67 (s, 2H), 6.85-6.91 (m, 2H), 7.31 (t, J=7.9 Hz, 1H), 7.36-7.43 (m, 2H).

Workup

  1. customThe ethanol was evaporated to dryness
  2. dissolutionthe crude product was dissolved in a minimum of dichloromethane
  3. extractionThe crude product was then extracted twice with 1M sodium hydroxide and once with a saturated aqueous solution of sodium chloride
  4. dry with materialThe organic layer was then dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-03ca044f273d493db87da3931fd217d1
Source dataset
uspto-grants-2014_10
Patent number
US08853415B2

Reaction notes

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