Benzyl Chloride → HCID 21497805, compound

HRID 1730416Notes

Reaction equation

HRID 1730416 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 andthe 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-d2154d7323f3458a8ce7690908c3c5ec
Source dataset
uspto-grants-1976_11
Patent number
US03992440

Reaction notes

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