Hydrochloric Acid → N-benzyl-N-(3-n-butylamino-4-phenoxy-5-sulfamylbenzyl)acetamide

HRID 2082898Notes

Reaction equation

HRID 2082898 reaction equation
[CH2:1]([NH:5][C:6]1[CH:7]=[C:8]([CH:18]=[C:19]([S:28](=[O:31])(=[O:30])[NH2:29])[C:20]=1[O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:9][NH:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:2][CH2:3][CH3:4].[OH2:32].Cl.N1[CH:39]=[CH:38]C=CC=1>C(OC(=O)C)(=O)C>[CH2:11]([N:10]([CH2:9][C:8]1[CH:18]=[C:19]([S:28](=[O:31])(=[O:30])[NH2:29])[C:20]([O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:6]([NH:5][CH2:1][CH2:2][CH2:3][CH3:4])[CH:7]=1)[C:38](=[O:32])[CH3:39])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 1049PyridineHCID 53795311(3-n-Butylamino-4-phenoxy-5-sulfamylbenzyl)benzylamine

Product 1

HCID 53734224N-benzyl-N-(3-n-butylamino-4-phenoxy-5-sulfamylbenzyl)acetamide

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

To a solution of (3-n-butylamino-4-phenoxy-5-sulfamylbenzyl)benzylamine (1.1 g; prepared as described in Example 136) in pyridine (6 ml), acetic anhydride (0.26 ml) is added and the mixture is left for 3 hours. Water (25 ml) is then added followed by concentrated hydrochloric acid (3 ml) to precipitate a semi-solid material. After recrystallization twice from aqueous ethanol, N-benzyl-N-(3-n-butylamino-4-phenoxy-5-sulfamylbenzyl)acetamide is obtained with a melting point of 75°-77° C.

Workup

  1. customto precipitate a semi-solid material
  2. customAfter recrystallization twice from aqueous ethanol

Sources & evidence

ORD record
ord-7e82cac508f749e0b0cb1cdcc027504a
Source dataset
uspto-grants-1978_04
Patent number
US04082851

Reaction notes

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