Propanethioamide → 4-[2-ethyl-4-(3-methylphenyl)-1,3-thiazol-5-yl]pyridin-2-amine

HRID 1268732Notes

Reaction equation

HRID 1268732 reaction equation
Br.[NH2:2][C:3]1[CH:8]=[C:7]([CH:9](Br)[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[CH:13]=2)=O)[CH:6]=[CH:5][N:4]=1.[C:20]([NH2:24])(=[S:23])[CH2:21][CH3:22]>CN(C)C=O>[CH2:21]([C:20]1[S:23][C:9]([C:7]2[CH:6]=[CH:5][N:4]=[C:3]([NH2:2])[CH:8]=2)=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[CH:13]=2)[N:24]=1)[CH3:22]

Participants

4

Reactant 2

HCID 2760628PropanethioamideHCID 219642042-(2-Amino-4-pyridyl)-2-bromo-1-(3-methylphenyl)ethanone hydrobromide

Product 1

HCID 98573494-[2-ethyl-4-(3-methylphenyl)-1,3-thiazol-5-yl]pyridin-2-amineYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-(2-amino-4-pyridyl)-2-bromo-1-(3-methylphenyl)ethanone hydrobromide (125 g, 0.323 mol) and thiopropionamide (28 g, 0.314 mol) in N,N-dimethylformamide (1200 mL) was stirred at room temperature for 14 hrs. The solvent was evaporated under reduced pressure. Aqueous sodium hydrogen carbonate solution was poured into the residue and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution, dried and concentrated. Crude crystals were washed with hexane-ethyl acetate=1:1 to give the title compound (76.0 g, yield 82%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionAqueous sodium hydrogen carbonate solution was poured into the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution
  5. customdried
  6. concentrationconcentrated
  7. washCrude crystals were washed with hexane-ethyl acetate=1:1

Sources & evidence

ORD record
ord-31a488da3a1947839a176a79e6843c55
Source dataset
uspto-grants-2007_04
Patent number
US07199124B2

Reaction notes

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