Aniline → HCID 54505847, compound

HRID 2082879Notes

Reaction equation

HRID 2082879 reaction equation
Br.[CH2:2]([NH:6][C:7]1[CH:8]=[C:9]([CH:12]=[C:13]([S:22](=[O:25])(=[O:24])[NH2:23])[C:14]=1[O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:10]Br)[CH2:3][CH2:4][CH3:5].[NH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CO.O>[CH2:2]([NH:6][C:7]1[CH:8]=[C:9]([CH:12]=[C:13]([S:22](=[O:25])(=[O:24])[NH2:23])[C:14]=1[O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:10][NH:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 2

HCID 6115AnilineHCID 70574272HCID 70574272, compound

Product 1

HCID 54505847HCID 54505847, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 3-n-butylamino-4-phenoxy-5-sulfamylbenzyl bromide hydrobromide (2.5 g; prepared as described in Example 67) and aniline (10 ml) in methanol (20 ml) is refluxed for 16 hours. After cooling the mixture is diluted with water (about 80 ml); the resulting semi-solid precipitate is washed twice with water, which is decanted, and is then crystallized from aqueous ethanol. After filtration and recrystallization from ethanol, (3-n-butylamino-4-phenoxy-5-sulfamylbenzyl)aniline is obtained with a melting point of 142°-143° C.

Workup

  1. temperatureAfter cooling the mixture
  2. washthe resulting semi-solid precipitate is washed twice with water, which
  3. customis decanted
  4. customis then crystallized from aqueous ethanol
  5. filtrationAfter filtration and recrystallization from ethanol

Sources & evidence

ORD record
ord-880e154513d84b7b88fae220d70c6544
Source dataset
uspto-grants-1978_04
Patent number
US04082851

Reaction notes

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