Phenyltrimethylammonium bromide dibromide → N-(4-(2-Bromoacetyl)-5-(3-(trifluoromethyl)phenyl)thiazol-2-yl)-2,6-difluorobenzamide

HRID 1255142Notes

Reaction equation

HRID 1255142 reaction equation
[C:1]([C:4]1[N:5]=[C:6]([NH:19][C:20](=[O:29])[C:21]2[C:26]([F:27])=[CH:25][CH:24]=[CH:23][C:22]=2[F:28])[S:7][C:8]=1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=1)(=[O:3])[CH3:2].[Br-:30].[Br-].[Br-].C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1>C1COCC1>[Br:30][CH2:2][C:1]([C:4]1[N:5]=[C:6]([NH:19][C:20](=[O:29])[C:21]2[C:26]([F:27])=[CH:25][CH:24]=[CH:23][C:22]=2[F:28])[S:7][C:8]=1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:16])([F:17])[F:18])[CH:10]=1)=[O:3]

Participants

4

Reactant 2

HCID 17977687Phenyltrimethylammonium bromide dibromideHCID 24765682N-(4-Acetyl-5-(3-(trifluoromethyl)phenyl)thiazol-2-yl)-2,6-difluorobenzamide

Product 1

HCID 24765772N-(4-(2-Bromoacetyl)-5-(3-(trifluoromethyl)phenyl)thiazol-2-yl)-2,6-difluorobenzamideYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Into a solution of Compound 84 (132 mg, 0.33 mmol) in THF (10 mL) at 0° C. was added phenyltrimethylammonium tribromide (125 mg, 0.33 mmol). The mixture was stirred at 0° C. for 1 hour, quenched by ice addition, extracted with methylene chloride. The combined extracted was dried (Na2SO4), filtered and concentrated. The residue was purified on silica (eluted with methylene chloride) to give Compound 85 (128 mg, 85%) as a white solid.

Workup

  1. customquenched by ice addition
  2. extractionextracted with methylene chloride
  3. extractionThe combined extracted
  4. dry with materialwas dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified on silica (eluted with methylene chloride)

Sources & evidence

ORD record
ord-cc5ddd4162374c4984608fdd2198e880
Source dataset
uspto-grants-2013_06
Patent number
US08455658B2

Reaction notes

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