Water → HCID 86690816, compound

HRID 1465515Notes

Reaction equation

HRID 1465515 reaction equation
[CH3:1][O:2][C:3]1[CH:26]=[CH:25][C:6]([O:7][C:8]2[CH:13]=[C:12]([CH3:14])[C:11]([C:15]3[N:16]=[C:17]([NH:20][C:21](=[O:23])[CH3:22])[S:18][CH:19]=3)=[C:10]([CH3:24])[CH:9]=2)=[CH:5][CH:4]=1.[Br:27]Br.O>C(O)(=O)C>[Br:27][C:19]1[S:18][C:17]([NH:20][C:21](=[O:23])[CH3:22])=[N:16][C:15]=1[C:11]1[C:10]([CH3:24])=[CH:9][C:8]([O:7][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:26][CH:25]=2)=[CH:13][C:12]=1[CH3:14]

Participants

5

Reactant 3

HCID 962WaterHCID 24408BromineHCID 86690814HCID 86690814, compound

Product 1

HCID 86690816HCID 86690816, compoundYield 94.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of N-{4-(4-(4-methoxyphenoxy)-2,6-dimethylphenyl)thiazol-2-yl}acetamide (2-2, 465 mg, 1.3 mmol) in acetic acid (10.2 mL) was added bromine (0.060 mL, 1.3 mmol) dropwisely. The reaction was stirred at room temperature for 4.0 h. The solution was added with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous MgSO4(s), and concentrated under reduced pressure to give N-{5-bromo-4-(4-(4-methoxyphenoxy)-2,6-dimethylphenyl)thiazol-2-yl}acetamide (2-3, 547 mg) as white solids, which was used directly for the next step without further purification.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous MgSO4(s)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7c4ebb3b661e4950a7210b43bab16650
Source dataset
uspto-grants-2015_04
Patent number
US08999983B2

Reaction notes

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