Hydrochloric Acid → 4-Chloro-N-[4-(2-methoxyphenyl)-1-piperazinyl]-3-sulfamoylbenzamide

HRID 1906243Notes

Reaction equation

HRID 1906243 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[Cl:16][C:17]1[CH:25]=[CH:24][C:20]([C:21]([OH:23])=O)=[CH:19][C:18]=1[S:26](=[O:29])(=[O:28])[NH2:27].[NH2:30][N:31]1[CH2:36][CH2:35][N:34]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=2[O:43][CH3:44])[CH2:33][CH2:32]1.Cl.[OH-].[Na+]>O1CCCC1>[Cl:16][C:17]1[CH:25]=[CH:24][C:20]([C:21]([NH:30][N:31]2[CH2:32][CH2:33][N:34]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=3[O:43][CH3:44])[CH2:35][CH2:36]2)=[O:23])=[CH:19][C:18]=1[S:26](=[O:29])(=[O:28])[NH2:27]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 10868DicyclohexylcarbodiimideHCID 145684-Chloro-3-sulfamoylbenzoic acidHCID 14798Sodium HydroxideHCID 137302004-(2-Methoxyphenyl)piperazin-1-amine

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1.8 g of N,N'-dicyclohexylcarbodiimide in 5 ml tetrahydrofuran was added a solution of 2.1 g of 4-chloro-3-sulfamoylbenzoic acid in 20 ml of tetrahydrofuran under stirring at room temperature. After the addition was completed, the mixture was stirred at room temperature for 20 minutes, then 0.83 g of 1-amino-4-(2-methoxyphenyl)piperazine was added, and the reaction mixture was stirred for 5 hours. Then 5 ml of 10% hydrochloric acid was added and stirred at room temperature for 10 minutes. 250 ml of 2% sodium hydroxide solution was added and insoluble materials were filtered off. The filtrate was alkalized with 2% sodium hydroxide solution to give white precipitate. The resulting precipitate was filtered, washed with water and recrystallized from ethanol to afford a title compound in a yield of 0.84 g (49%) as colorless crystals, mp 232°-235° C.

Workup

  1. additionAfter the addition
  2. stirringthe mixture was stirred at room temperature for 20 minutes
  3. stirringthe reaction mixture was stirred for 5 hours
  4. stirringstirred at room temperature for 10 minutes
  5. filtrationinsoluble materials were filtered off
  6. customto give white precipitate
  7. filtrationThe resulting precipitate was filtered
  8. washwashed with water
  9. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-411647cc998e4d4ca62539f7a7fc43cd
Source dataset
uspto-grants-1987_03
Patent number
US04650871

Reaction notes

Loading…