Sodium Hydroxide → HCID 53651032, compound

HRID 1580824Notes

Reaction equation

HRID 1580824 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[C:20]([S:21](=[O:24])(=[O:23])[NH2:22])=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[CH:14][C:13]=2[NH2:25])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].Br[CH2:27][CH:28]=[CH:29][CH3:30].[OH-].[Na+]>O>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[C:20]([S:21](=[O:23])(=[O:24])[NH2:22])=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[CH:14][C:13]=2[NH:25][CH2:27][CH:28]=[CH:29][CH3:30])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 1224142-Butene, 1-bromo-HCID 21563898HCID 21563898, compound

Product 1

HCID 53651032HCID 53651032, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The starting material is prepared as follows: To the stirred mixture of 5.5 g of 4-(4-acetamidophenylamino)-3-amino-5-sulfamoylbenzoic acid, 2.0 g of 1-bromo-2-butene, 30 ml of water and 10 ml of N aqueous sodium hydroxide, 4N aqueous sodium hydroxide is added dropwise in order to keep the pH of the mixture at 7.4 for 17 hours. It is filtered, the filtrate acidified with glacial acetic acid to pH = 4 and the precipitate formed filtered off. It is recrystallized from aqueous ethanol, to yield the 4-(4-acetamidophenylamino)-3-but-2-enylamino-5-sulfamoylbenzoic acid melting at about 230° with decomposition.

Workup

  1. customThe starting material is prepared
  2. additionis added dropwise in order
  3. customfor 17 hours
  4. filtrationIt is filtered
  5. customthe precipitate formed
  6. filtrationfiltered off
  7. customIt is recrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-d6d1a84123b84833ab764318e8187de1
Source dataset
uspto-grants-1976_01
Patent number
US03933906

Reaction notes

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