Hydrochloric Acid → N-(2-benzoyl-4-chloro-phenyl)-4-bromo-benzenesulfonamide

HRID 18896

Reaction equation

HRID 18896 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].[Br:17][C:18]1[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1.Cl>N1C=CC=CC=1.CCOC(C)=O.O>[C:4]([C:3]1[CH:12]=[C:13]([Cl:16])[CH:14]=[CH:15][C:2]=1[NH:1][S:24]([C:21]1[CH:22]=[CH:23][C:18]([Br:17])=[CH:19][CH:20]=1)(=[O:26])=[O:25])(=[O:5])[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 7396p-Bromobenzenesulfonyl chlorideHCID 128702-Amino-5-chlorobenzophenone

Product 1

HCID 3334757N-(2-benzoyl-4-chloro-phenyl)-4-bromo-benzenesulfonamideYield 98.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Amino-5-chlorobenzophenone (5.33 g, 23 mmol) was dissolved in 100 mL pyridine and stirred at room temperature. 4-Bromobenzenesulfonyl chloride (6.17 g, 24.1 mmol) was added and the mixture was stirred overnight. The mixture was poured in a steady stream into 350 mL vigorously stirring chilled 6M HCl which resulted in the precipitation of a reddish oil. The solution was diluted with 100 mL EtOAc and 200 mL H2O, shaken in a separating funnel and the aqueous layer discarded. The organics were dried and reduced in vacuo to yield title compound (10.2 g, 98%). 1H NMR (400 MHz, CDCl3): δ 7.34 (m, 5H), 7.43-7.48 (m, 5H), 7.62 (t, 1H), 7.74 (d, 1H), 9.62 (s, 1H). MS: m/z=449.9 (M++1).

Workup

  1. stirringthe mixture was stirred overnight
  2. additionThe mixture was poured in a steady stream into 350 mL
  3. stirringvigorously stirring
  4. customresulted in the precipitation of a reddish oil
  5. stirringshaken in a separating funnel
  6. customThe organics were dried

Sources & evidence

ORD record
ord-26c50f35ca01425f953f3b1789ffe2e9
Source dataset
uspto-grants-2010_06
Patent number
US07741519B2

Linked notes

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