Benzenesulfonyl chloride → HCID 10763869, compound

HRID 745072Notes

Reaction equation

HRID 745072 reaction equation
[NH2:1][C:2]1[CH:20]=[CH:19][C:5]([C:6]([N:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[CH2:12][CH2:11][CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1.[C:21]1([S:27](Cl)(=[O:29])=[O:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(N(CC)CC)C>ClCCl>[C:21]1([S:27]([NH:1][C:2]2[CH:20]=[CH:19][C:5]([C:6]([N:8]3[C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=4[CH2:12][CH2:11][CH2:10][CH2:9]3)=[O:7])=[CH:4][CH:3]=2)(=[O:29])=[O:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 10587836(4-aminophenyl)-(2,3,4,5-tetrahydro-1-benzazepin-1-yl)methanone

Product 1

HCID 10763869HCID 10763869, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-(4-aminobenzoyl)-2,3,4,5-tetrahydro-1H-benzazepine (0.50 g), phenylsulfonyl chloride (0.29 ml), triethylamine (0.32 ml) and dichloromethane (30 ml) is stirred at room temperature overnight. The reaction mixture is washed successively with water and saturated saline solution, and dried over magnesium sulfate. The solvent is distilled off and the resulting residue is purified by silica gel column chromatography (eluent; chloroform), and recrystallized from methanol/diethyl ether to give 1-(4-phenylsulfonylaminobenzoyl)-2,3,4,5-tetrahydro-1H-benzazepine (0.27 g) as colorless prisms, m.p. 178°-182.5° C.

Workup

  1. washThe reaction mixture is washed successively with water and saturated saline solution
  2. dry with materialdried over magnesium sulfate
  3. distillationThe solvent is distilled off
  4. customthe resulting residue is purified by silica gel column chromatography (eluent; chloroform)
  5. customrecrystallized from methanol/diethyl ether

Sources & evidence

ORD record
ord-d0c3059ae150482daa39cb592596c528
Source dataset
uspto-grants-1996_09
Patent number
US05559230

Reaction notes

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