Water → HCID 54468105, compound

HRID 1576728Notes

Reaction equation

HRID 1576728 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S: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].O.[OH-].[Li+].[CH:29]1([CH2:32]Br)[CH2:31][CH2:30]1>C(O)C>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S: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[NH:25][CH2:32][CH:29]2[CH2:31][CH2:30]2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 3939Lithium Hydroxide2×HCID 81503BromomethylcyclopropaneHCID 54216006HCID 54216006, compound

Product 1

HCID 54468105HCID 54468105, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The starting material is prepared as follows: To the mixture of 3.8 g of 4-(4-acetamidophenylmercapto)-3-amino-5-sulfamoylbenzoic acid, 20 ml of water, 15 ml of ethanol and 2 ml of 4 N aqueous lithium hydroxide, 2.2 g, of cyclopropylmethyl bromide are added while stirring and the pH of the mixture adjusted with lithium hydroxide to 7.0 during 24 hours. Thereupon, it is filtered, the filtrate diluted with water, washed with diethyl ether and acidified with concentrated hydrochloric acid. The precipitate formed is filtered off and recrystallized from aqueous ethanol, to yield the 4-(4-acetamidophenylmercapto)-3-cyclopropylmethylamino-5-sulfamoylbenzoic acid melting at 200°-204°.

Workup

  1. customThe starting material is prepared
  2. filtrationThereupon, it is filtered
  3. additionthe filtrate diluted with water
  4. washwashed with diethyl ether
  5. customThe precipitate formed
  6. filtrationis filtered off
  7. customrecrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-a3af94b4f9684d9b9ba975d4e5953a5a
Source dataset
uspto-grants-1976_09
Patent number
US03982018

Reaction notes

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