Benzyl Chloride → HCID 21497805, compound

HRID 1576716Notes

Reaction equation

HRID 1576716 reaction equation
[C:1]([NH:4][C:5]1[CH:25]=[CH:24][C:8]([O:9][C:10]2[C:18]([S:19](=[O:22])(=[O:21])[NH2:20])=[CH:17][C:13]([C:14]([OH:16])=[O:15])=[CH:12][C:11]=2[NH2:23])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[OH-].[Na+].[CH2:28](Cl)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>O>[C:1]([NH:4][C:5]1[CH:25]=[CH:24][C:8]([O:9][C:10]2[C:18]([S:19](=[O:21])(=[O:22])[NH2:20])=[CH:17][C:13]([C:14]([OH:16])=[O:15])=[CH:12][C:11]=2[NH:23][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 14798Sodium Hydroxide2×HCID 214978384-(4-Acetamidophenoxy)-3-amino-5-sulfamoylbenzoic acid

Product 1

HCID 21497805HCID 21497805, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The starting material is prepared as follows: To the mixture of 3.6 g of 4-(4-acetamidophenoxy)-3-amino-5-sulfamoylbenzoic acid, 10 ml of water and the sufficient amount of N aqueous sodium hydroxide to reach a pH = 7.4, 1.3 g of benzyl chloride are added while stirring at 30°. The mixture is stirred for 16 hours at room temperature, during which time 4N aqueous sodium hydroxide is added dropwise to keep said pH value. It is filtered, the filtrate acidified with glacial acetic acid and the precipitate formed filtered off, to yield the 4-(4-acetamidophenoxy)-3-benzylamino-5-sulfamoylbenzoic acid which, on recrystallization from aqueous ethanol, melts at 255° with decomposition.

Workup

  1. customThe starting material is prepared
  2. additionare added
  3. additionis added dropwise
  4. filtrationIt is filtered
  5. customthe precipitate formed
  6. filtrationfiltered off

Sources & evidence

ORD record
ord-d519f5143dc444e8a0893f9ffa34daef
Source dataset
uspto-grants-1976_09
Patent number
US03982018

Reaction notes

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