Benzyl Bromide → HCID 21506112, compound

HRID 918690Notes

Reaction equation

HRID 918690 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([S:16](=[O:19])(=[O:18])[NH2:17])[C:10]=1[NH:11][CH2:12][CH2:13][CH2:14][CH3:15])[C:5]([OH:7])=[O:6].[OH-].[Na+].[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>O>[CH2:22]([NH:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([S:16](=[O:19])(=[O:18])[NH2:17])[C:10]=1[NH:11][CH2:12][CH2:13][CH2:14][CH3:15])[C:5]([OH:7])=[O:6])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 14798Sodium Hydroxide2×HCID 21506070HCID 21506070, compound

Product 1

HCID 21506112HCID 21506112, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of 3-amino-4-butylamino-5-sulphamyl-benzoic acid (6.5 g) in water (30 ml) was adjusted to pH 7.5 H by addition of 1N sodium hydroxide. Benzyl bromide (3.87 g) was added and, under stirring, the pH was kept at pH 7.5 by automatic titration with 1N sodium hydroxide. After the base consumption had become negligible, the pH was adjusted to 3 by addition of diluted hydrochloric acid. The precipitated 3-benzylamino-4-butylamino-5-sulphamyl-benzoic acid was collected and recrystallized several times from aqueous methanol, after which the compound was obtained with a melting point of 198.5-199°C.

Workup

  1. customAfter the base consumption
  2. additionthe pH was adjusted to 3 by addition of diluted hydrochloric acid
  3. customThe precipitated 3-benzylamino-4-butylamino-5-sulphamyl-benzoic acid was collected
  4. customrecrystallized several times from aqueous methanol
  5. customafter which the compound was obtained with a melting point of 198.5-199°C.

Sources & evidence

ORD record
ord-a2508dedd1a74520a61895b67d1253f2
Source dataset
uspto-grants-1976_07
Patent number
US03971819

Reaction notes

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