Lithium Hydroxide → HCID 21499013, compound

HRID 1287772Notes

Reaction equation

HRID 1287772 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([S:18](=[O:21])(=[O:20])[NH2:19])[C:10]=1[S:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:5]([OH:7])=[O:6].[OH-].[Li+].[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>O>[CH2:24]([NH:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([S:18](=[O:20])(=[O:21])[NH2:19])[C:10]=1[S:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:5]([OH:7])=[O:6])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 3939Lithium Hydroxide2×HCID 7498Benzyl BromideHCID 21312193HCID 21312193, compound

Product 1

HCID 21499013HCID 21499013, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of 3-amino-4-phenylthio-5-sulphamyl-benzoic acid (4.05 g) in water (100 ml) was adjusted to pH 7.5 by addition of 1N lithium hydroxide. Benzyl bromide (2.2 g) was added and, under stirring, the pH was kept at 7.5 by automatic titration with lithium hydroxide. After the base consumption had become negligible, the pH was adjusted to 2.5 by addition of dilute hydrochloric acid. The precipitated 3-benzylamino-4-phenylthio-5-sulphamyl-benzoic acid was collected and recrystallized from ethanol, whereafter the compound was obtained with a melting point of 224°-225° C.

Workup

  1. customAfter the base consumption
  2. additionthe pH was adjusted to 2.5 by addition of dilute hydrochloric acid
  3. customThe precipitated 3-benzylamino-4-phenylthio-5-sulphamyl-benzoic acid was collected
  4. customrecrystallized from ethanol, whereafter the compound
  5. customwas obtained with a melting point of 224°-225° C.

Sources & evidence

ORD record
ord-93130c2da63b48b5a6f44e17ed2463c2
Source dataset
uspto-grants-1976_10
Patent number
US03985777

Reaction notes

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