Ethanol → Ethyl 3-benzylamino-5-sulphamyl-4-(m-toluidino)-benzoate

HRID 918684Notes

Reaction equation

HRID 918684 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([S:19](=[O:22])(=[O:21])[NH2:20])[C:10]=1[NH:11][C:12]1[CH:13]=[C:14]([CH3:18])[CH:15]=[CH:16][CH:17]=1)[C:5]([OH:7])=[O:6].[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[CH2:31](O)[CH3:32]>>[CH2:23]([NH:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([S:19](=[O:22])(=[O:21])[NH2:20])[C:10]=1[NH:11][C:12]1[CH:13]=[C:14]([CH3:18])[CH:15]=[CH:16][CH:17]=1)[C:5]([O:7][CH2:31][CH3:32])=[O:6])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 7498Benzyl BromideHCID 21506124Benzoic acid,3-amino-5-(aminosulfonyl)-4-[(3-methylphenyl)amino]-

Product 1

HCID 21506091Ethyl 3-benzylamino-5-sulphamyl-4-(m-toluidino)-benzoate

Procedure

A mixture of 3-amino-5-sulphamyl-4-(m-toluidino)-benzoic acid (1.5 g), benzyl bromide (2.5 g), and anhydrous ethanol (50 ml) was heated under reflux for 10 hours. The resulting solution was cooled, and the precipitated ethyl 3-benzylamino-5-sulphamyl-4-(m-toluidino)-benzoate was collected by suction. After recrystallization from ethanol, the compound had a melting point of 169-170°C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 10 hours
  3. temperatureThe resulting solution was cooled
  4. customthe precipitated ethyl 3-benzylamino-5-sulphamyl-4-(m-toluidino)-benzoate was collected by suction
  5. customAfter recrystallization from ethanol

Sources & evidence

ORD record
ord-6fc8ca009fb34cd3b0c96a181fc5afb2
Source dataset
uspto-grants-1976_07
Patent number
US03971819

Reaction notes

Loading…