Water → HCID 20364661, compound

HRID 225777

Reaction equation

HRID 225777 reaction equation
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:9]1[S:10][C:11]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:12]([CH3:14])[N:13]=1.O>CN(C)C=O>[CH3:14][C:12]1[N:13]=[C:9]([S:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[S:10][C:11]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

5

Reactant 3

HCID 962WaterHCID 7969ThiophenolHCID 594903Ethyl 2-chloro-4-methyl-1,3-thiazole-5-carboxylate

Product 1

HCID 20364661HCID 20364661, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Thiophenol (1.90 ml) was dissolved in N,N-dimethylformamide (10 ml) Sodium hydride (60% oil suspension, 740 mg) was added by portions under ice-cooling, and the mixture was stirred at room temperature for 15 min. Thereafter, a solution of ethyl 2-chloro-4-methylthiazole-5-carboxylate (3.05 g) in N,N-dimethylformamide (10 ml) was added dropwise, and the mixture was stirred at the same temperature for 20 min. Water (50 ml) was added to the reaction mixture, and the mixture was extracted with ethyl acetate (50 ml). The ethyl acetate layer was washed twice with water (50 ml) and then with saturated brine (30 ml), and dried (Na2SO4). Ethyl acetate was evaporated under reduced pressure and the obtained residue was purified by column chromatography to give ethyl 4-methyl-2-phenylsulfanylthiazole-5-carboxylate (3.85 g).

Workup

  1. additionwas added by portions under ice-
  2. temperaturecooling
  3. stirringthe mixture was stirred at the same temperature for 20 min
  4. extractionthe mixture was extracted with ethyl acetate (50 ml)
  5. washThe ethyl acetate layer was washed twice with water (50 ml)
  6. dry with materialwith saturated brine (30 ml), and dried (Na2SO4)
  7. customEthyl acetate was evaporated under reduced pressure
  8. customthe obtained residue was purified by column chromatography

Sources & evidence

ORD record
ord-d4501c3e611d4c658621a081bd183b26
Source dataset
uspto-grants-2009_07
Patent number
US07557123B2

Linked notes

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