Benzenesulfonyl chloride → N-(5-Acetyl-2-benzyloxy-phenyl)-benzenesulfonamide

HRID 1061214Notes

Reaction equation

HRID 1061214 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:16](=[O:18])[CH3:17])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[C:19]1([S:25](Cl)(=[O:27])=[O:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>N1C=CC=CC=1.C(Cl)Cl>[C:16]([C:4]1[CH:5]=[CH:6][C:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:2]([NH:1][S:25]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)(=[O:27])=[O:26])[CH:3]=1)(=[O:18])[CH3:17]

Participants

5

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 155794401-[3-Amino-4-(benzyloxy)phenyl]ethan-1-one

Product 1

HCID 22220572N-(5-Acetyl-2-benzyloxy-phenyl)-benzenesulfonamideYield 47%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1-(3-amino-4-benzyloxy-phenyl)-ethanone (EP 0 659 737) (16.98 g, 70.0 mmol) in pyridine (50 mL) was added dropwise benzenesulfonyl chloride (13.09 g, 73.5 mmol) in 100 mL of pyridine at room temperature. The reaction was stirred for 18 hours under nitrogen atmosphere. The mixture was diluted with CH2Cl2 (700 mL) and washed with 1N hydrochloric acid, water, dried over Na2SO4, and concentrated. The product was purified by flash silica gel chromatography eluting with CH2Cl2 to give the title compound as a tan solid (12.55 g, 47%); 1H NMR (300 MHz, DMSO-d6) δ 3.33 (s, 3H), 5.03 (s, 2H), 7.02 (d, J=8.7 Hz, 1H), 7.35 (m, 3H), 7.44 (t, J=15 Hz, 2H), 7.58 (m, 1H), 7.50 (m, 3H), 7.81 (d, 1H), 9.83 (s, 1H); MS (ES) m/z: 381.9 (MH+, 100%); HRMS Calcd. for C21H19NO4S(MH+): 382.1107. Found: 382.1100.

Workup

  1. washwashed with 1N hydrochloric acid, water
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customThe product was purified by flash silica gel chromatography
  5. washeluting with CH2Cl2

Sources & evidence

ORD record
ord-a9e70929f0344781bd62c55b528a9c6b
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

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