Acetic Acid → N-(3-n-Butylamino-4-phenoxy-5-sulfamylbenzyl)acetamide

HRID 1390074Notes

Reaction equation

HRID 1390074 reaction equation
[CH2:1]([NH:5][C:6]1[CH:7]=[C:8]([CH:11]=[C:12]([S:21](=[O:24])(=[O:23])[NH2:22])[C:13]=1[O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:9][NH2:10])[CH2:2][CH2:3][CH3:4].[C:25](O)(=[O:27])[CH3:26]>C(OC(=O)C)(=O)C>[CH2:1]([NH:5][C:6]1[CH:7]=[C:8]([CH:11]=[C:12]([S:21](=[O:24])(=[O:23])[NH2:22])[C:13]=1[O:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[CH2:9][NH:10][C:25](=[O:27])[CH3:26])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 540392965-(Aminomethyl)-3-(butylamino)-2-phenoxybenzene-1-sulfonamide

Product 1

HCID 53985487N-(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-sulfamylbenzylamine (1.05 g; prepared as described in Example 289) in acetic acid (10 ml), acetic anhydride (0.4 ml) is added and the mixture is left for 24 hours. Dilution with water (25 ml) precipitates N-(3-n-butylamino-4-phenoxy-5-sulfamylbenzyl)acetamide, which is collected by filtration, washed with water and dried in air. After recrystallization from aqueous ethanol it is obtained with a melting point of 190°-191° C.

Workup

  1. customDilution with water (25 ml) precipitates N-(3-n-butylamino-4-phenoxy-5-sulfamylbenzyl)acetamide, which
  2. filtrationis collected by filtration
  3. washwashed with water
  4. customdried in air
  5. customAfter recrystallization from aqueous ethanol it
  6. customis obtained with a melting point of 190°-191° C.

Sources & evidence

ORD record
ord-c230f020fef742a2b9c9b5abd06a11c8
Source dataset
uspto-grants-1981_01
Patent number
US04247550

Reaction notes

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