Benzyl Bromide → 3-Benzylamino-4-(beta-phenylethylamino)-5-sulphamyl-benzoic acid

HRID 918680Notes

Reaction equation

HRID 918680 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([S:20](=[O:23])(=[O:22])[NH2:21])[C:10]=1[NH:11][CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:5]([OH:7])=[O:6].[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(O)C>[CH2:24]([NH:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([S:20](=[O:23])(=[O:22])[NH2:21])[C:10]=1[NH:11][CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:5]([OH:7])=[O:6])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 125913993-Amino-4-(beta-phenylethylamino)-5-sulphamyl-benzoic acid

Product 1

HCID 215059893-Benzylamino-4-(beta-phenylethylamino)-5-sulphamyl-benzoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-amino-4-(β-phenylethylamino)-5-sulphamyl-benzoic acid (3.35 g), benzyl bromide (5.3 g), and anhydrous ethanol (30 ml) was refluxed for 48 hours. After cooling, the precipitated ethyl ester was collected by suction, recrystallized from ethanol and saponified by heating in 1N sodium hydroxide (30 ml) for 1 hour. The 3-benzylamino-4-(β-phenylethylamino)-5-sulphamyl-benzoic acid was precipitated at room temperature by addition of 4N hydrochloric acid until the pH was 2.5. After recrystallization from aqueous ethanol, the compound was obtained with a melting point of 203°C.

Workup

  1. temperaturewas refluxed for 48 hours
  2. temperatureAfter cooling
  3. customthe precipitated ethyl ester was collected by suction
  4. customrecrystallized from ethanol
  5. temperaturesaponified by heating in 1N sodium hydroxide (30 ml) for 1 hour
  6. customThe 3-benzylamino-4-(β-phenylethylamino)-5-sulphamyl-benzoic acid was precipitated at room temperature by addition of 4N hydrochloric acid until the pH was 2.5
  7. customAfter recrystallization from aqueous ethanol
  8. customthe compound was obtained with a melting point of 203°C.

Sources & evidence

ORD record
ord-2cf7ce1fc3b34b27997cf0097ccf2338
Source dataset
uspto-grants-1976_07
Patent number
US03971819

Reaction notes

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