2-Amino-5-chlorobenzophenone → N-(2-benzoyl-4-chlorophenyl)trifluoromethanesulfonamide

HRID 602613Notes

Reaction equation

HRID 602613 reaction equation
[NH2:1][C:2]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].[O:17](S(C(F)(F)F)(=O)=O)[S:18]([C:21]([F:24])([F:23])[F:22])(=O)=[O:19]>C(Cl)Cl>[C:4]([C:3]1[CH:12]=[C:13]([Cl:16])[CH:14]=[CH:15][C:2]=1[NH:1][S:18]([C:21]([F:24])([F:23])[F:22])(=[O:19])=[O:17])(=[O:5])[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 128702-Amino-5-chlorobenzophenoneHCID 67749Trifluoromethanesulfonic anhydride

Product 1

HCID 67271057N-(2-benzoyl-4-chlorophenyl)trifluoromethanesulfonamideYield 90.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-amino-5-chlorobenzophenone (500 mg, 2.16 mmol) in anhydrous CH2Cl2 (30 mL) at 0° C. was added dropwise (CF3SO2)2O (545 μL, 3.24 mmol) in anhydrous CH2Cl2 (10 mL) over 10 min and the reaction allowed to warm to RT over 15 hours. The reaction mixture was washed with water, dried over MgSO4 and concentrated under vacuum. The residue was filtered through a pad of silica (eluting with CH2Cl2/PE, 7:3) to afford N-(2-benzoyl-4-chlorophenyl)trifluoromethanesulfonamide 25 (710 mg, 90%), as a pale yellow solid. 1H n.m.r. (200 MHz, CDCl3) δ 7.80-7.69, m, 3H, 7.66-7.51, m, 5H. HRMS (M+) 362.9928.

Workup

  1. washThe reaction mixture was washed with water
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated under vacuum
  4. filtrationThe residue was filtered through a pad of silica (eluting with CH2Cl2/PE, 7:3)

Sources & evidence

ORD record
ord-8f24989fabba48518075978627b6d6fe
Source dataset
uspto-grants-2011_03
Patent number
US07906538B2

Reaction notes

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