Thionyl Chloride → N-(4-Benzoyl-2-bromophenyl)-3,3,3,-trifluoro-2-hydroxy-2-methylpropanamide

HRID 374880Notes

Reaction equation

HRID 374880 reaction equation
[F:1][C:2]([F:10])([F:9])[C:3]([OH:8])([CH3:7])[C:4](O)=[O:5].S(Cl)(Cl)=O.[Br:15][C:16]1[CH:17]=[C:18]([CH:27]=[CH:28][C:29]=1[NH2:30])[C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:20]>CN(C)C(=O)C>[C:19]([C:18]1[CH:27]=[CH:28][C:29]([NH:30][C:4](=[O:5])[C:3]([OH:8])([CH3:7])[C:2]([F:10])([F:9])[F:1])=[C:16]([Br:15])[CH:17]=1)(=[O:20])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 27751253,3,3-Trifluoro-2-hydroxy-2-methylpropanoic acidHCID 10754901HCID 10754901, compound

Product 1

HCID 9909807N-(4-Benzoyl-2-bromophenyl)-3,3,3,-trifluoro-2-hydroxy-2-methylpropanamideYield 38%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a stirred, cooled (-20° C.) solution of 3,3,3-trifluoro-2-hydroxy-2-methylpropanoic acid (0.75 g) in N,N-dimethylacetamide (10 mL) was rapidly added thionyl chloride (0.56 g) and the mixture stirred at -15° to -20° C. for 1 hour. 3-Bromo-4-aminobenzophenone (0.75 g) was then added in one portion and the mixture was allowed to stir at room temperature overnight. The solution was poured into ice water and the aqueous phase decanted from the resulting oily solid. Chromatography (eluent methylene chloride) gave the title compound (0.43 g) as a white solid; mp 138°-40° C. Analysis for C17H13BrF3NO3 : Calculated: C, 49.06; H, 3.15; N, 3.37; Found: C, 49.06; H, 3.10; N, 3.35.

Workup

  1. stirringto stir at room temperature overnight
  2. customthe aqueous phase decanted from the resulting oily solid

Sources & evidence

ORD record
ord-fc4f28540fd84c398683d2e30e293914
Source dataset
uspto-grants-1996_01
Patent number
US05482969

Reaction notes

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