3-(Aminosulfonyl)-4-chlorobenzoyl chloride → 4-Chloro-N-[4-(2-methoxyphenyl)-1-piperazinyl]-3-sulfamoylbenzamide

HRID 1906244Notes

Reaction equation

HRID 1906244 reaction equation
[NH2:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[O:14][CH3:15])[CH2:4][CH2:3]1.[Cl:16][C:17]1[CH:25]=[CH:24][C:20]([C:21](Cl)=[O:22])=[CH:19][C:18]=1[S:26](=[O:29])(=[O:28])[NH2:27]>C(N(CC)CC)C>[Cl:16][C:17]1[CH:25]=[CH:24][C:20]([C:21]([NH:1][N:2]2[CH2:3][CH2:4][N:5]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[O:14][CH3:15])[CH2:6][CH2:7]2)=[O:22])=[CH:19][C:18]=1[S:26](=[O:28])(=[O:29])[NH2:27]

Participants

4

Reactant 2

HCID 30179793-(Aminosulfonyl)-4-chlorobenzoyl chlorideHCID 137302004-(2-Methoxyphenyl)piperazin-1-amine

Product 1

HCID 137302014-Chloro-N-[4-(2-methoxyphenyl)-1-piperazinyl]-3-sulfamoylbenzamide

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a mixture of 1 g of 1-amino-4-(2-methoxyphenyl)piperazine and 1 ml of triethylamine was added 1.25 g of 4-chloro-3-sulfamoylbenzoyl chloride under stirring at room temperature. The reaction mixture was stirred at room temperature for 9 hours. The resulting precipitate was filtered, washed with water and recrystallized from ethanol to afford a title compound in a yield of 1.20 g (60%) as colorless needle crystals, mp 231°-233° C.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 9 hours
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with water
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-940e105c96124fa69662da1fd4464f7d
Source dataset
uspto-grants-1987_03
Patent number
US04650871

Reaction notes

Loading…