Dichloromethane → N-[4-(4-bromophenyl)-1,3-thiazol-2-yl]-2-hydroxyacetamide

HRID 1436410Notes

Reaction equation

HRID 1436410 reaction equation
C([O:4][CH2:5][C:6]([NH:8][C:9]1[S:10][CH:11]=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][CH:15]=2)[N:13]=1)=[O:7])(=O)C.C([O-])([O-])=O.[K+].[K+].C(Cl)Cl>CO>[Br:20][C:17]1[CH:16]=[CH:15][C:14]([C:12]2[N:13]=[C:9]([NH:8][C:6](=[O:7])[CH2:5][OH:4])[S:10][CH:11]=2)=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 866186042-{[4-(4-Bromophenyl)-1,3-thiazol-2-yl]amino}-2-oxoethyl acetate

Product 1

HCID 790230N-[4-(4-bromophenyl)-1,3-thiazol-2-yl]-2-hydroxyacetamideYield 69%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-{[4-(4-Bromophenyl)-1,3-thiazol-2-yl]amino}-2-oxoethyl acetate (1.1 g, 3.1 mmol), prepared in the previous step, was suspended in 20 mL of methanol and K2CO3 (0.43 g, 3.1 mmol) was added. The mixture was stirred for 2 h, then diluted using methylene chloride. The mixture was washed with water, brine, dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. Flash chromatography (2% methanol/chloroform) provided N-[4-(4-bromophenyl)-1,3-thiazol-2-yl]-2-hydroxyacetamide (670 mg, 68%) as a white solid. mp 222-224° C. HRMS: calcd for C11H9BrN2O2S+H+, 312.96408; found (ESI, [M+H]+), 312.9651. Analytical HPLC: retention time 9.0 min, 210-370 nm the Xterra® RP18 column, 3.5μ, 150×4.6 mm 40° C. 85/15-5/95 (Ammon. Form. Buff. pH=3.5/ACN+MeOH) for 10 min, hold 4 min, 1.2 mL/min 5 μL injection.

Workup

  1. additiondiluted
  2. washThe mixture was washed with water, brine
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-eecb1eeb59564dcc8725ccceb39d3303
Source dataset
uspto-grants-2009_11
Patent number
US07618990B2

Reaction notes

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