Methanesulfonyl chloride → HCID 19608197, compound

HRID 1603123Notes

Reaction equation

HRID 1603123 reaction equation
O[CH:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]([C:13](=[O:30])[C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21](=[O:29])[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[CH3:28])=[CH:16][CH:15]=2)[CH2:5][CH2:4][CH2:3]1.CS([Cl:35])(=O)=O>ClCCl.N1C=CC=CC=1>[Cl:35][CH:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]([C:13](=[O:30])[C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21](=[O:29])[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[CH3:28])=[CH:16][CH:15]=2)[CH2:5][CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 10715974HCID 10715974, compound

Product 1

HCID 19608197HCID 19608197, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

5-Hydroxy-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (3.57 g) is dissolved in dichloromethane (30 ml) and pyridine (1.1 ml), and thereto is added dropwise methanesulfonyl chloride (0.9 ml) in small portions at 0° C. Then, the mixture is stirred at room temperature for 3 days. The solvent is distilled off and the resulting residue is poured into ice-water. The precipitated crystal is collected by filtration, washed with water, and dried to give 5-chloro-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (3.10 g) as light yellow powder.

Workup

  1. distillationThe solvent is distilled off
  2. additionthe resulting residue is poured into ice-water
  3. filtrationThe precipitated crystal is collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-d51538d552904526b381746343e1007c
Source dataset
uspto-grants-1999_11
Patent number
US05985869

Reaction notes

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