Ethanol → HCID 12085653, compound

HRID 747398Notes

Reaction equation

HRID 747398 reaction equation
Br[CH:2]([C:11](=O)[C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)[CH2:3][CH2:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7].[NH2:20][C:21]([NH2:23])=[S:22].C(O)C>O>[NH2:23][C:21]1[S:22][C:2]([CH2:3][CH2:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])=[C:11]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[N:20]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 2723790ThioureaHCID 12085652HCID 12085652, compound

Product 1

HCID 12085653HCID 12085653, compoundYield 89.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of ethyl 5-bromo-5-(4-chlorobenzoyl)valerate (17.4 g), thiourea (4.57 g) and ethanol (50 ml) was stirred with heating under reflux for 2 hours. The reaction mixture was poured into water (200 ml) and extracted with ethyl acetate (200 ml×2). The organic layer was dried over anhydrous magnesium sulfate and concentrated. The residue was recrystallized from ethanol to give ethyl 2-amino-4-(4-chlorophenyl)-5-thiazolebutanoate (14.6 g, 85%) as pale yellow prisms. Melting point 114-115° C.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 2 hours
  3. extractionextracted with ethyl acetate (200 ml×2)
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-49ff42a1bd934af188ac95bb792dda88
Source dataset
uspto-grants-2008_07
Patent number
US07396848B1

Reaction notes

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