Lithium Hydroxide → HCID 21506060, compound

HRID 1287795Notes

Reaction equation

HRID 1287795 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[N:17]=[C:16]([CH3:18])[CH:15]=[CH:14][CH:13]=1)[C:5]([OH:7])=[O:6].[OH-].[Li+].[CH2:25](Br)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>O>[CH2:25]([NH:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([S:19](=[O:21])(=[O:22])[NH2:20])[C:10]=1[NH:11][C:12]1[N:17]=[C:16]([CH3:18])[CH:15]=[CH:14][CH:13]=1)[C:5]([OH:7])=[O:6])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 3939Lithium Hydroxide2×HCID 7498Benzyl BromideHCID 21506043HCID 21506043, compound

Product 1

HCID 21506060HCID 21506060, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of 3-amino-4-(2-methyl-6-pyridylamino)-5-sulphamyl-benzoic acid (0.5 g) in water (25 ml) was adjusted to a pH of 8 by addition of 1N lithium hydroxide. To the resulting solution, benzyl bromide (0.2 g) was added while, under stirring, the pH was kept at 8 by automatic titration with 1N lithium hydroxide. After the base consumption had become negligible, the crude 3-benzylamino-4-(2-methyl-6-pyridylamino)-5-sulphamyl-benzoic acid was precipitated from the reaction mixture by adjusting the pH to 5 by means of 1N hydrochloric acid. The compound was collected by suction, recrystallized from aqueous ethanol, and dried. The melting point of the compound was 168°-170° C.

Workup

  1. customAfter the base consumption
  2. customthe crude 3-benzylamino-4-(2-methyl-6-pyridylamino)-5-sulphamyl-benzoic acid was precipitated from the reaction mixture
  3. customThe compound was collected by suction
  4. customrecrystallized from aqueous ethanol
  5. customdried
  6. customwas 168°-170° C.

Sources & evidence

ORD record
ord-4f20d1f3c9214c9bb4ca766730d9d999
Source dataset
uspto-grants-1976_10
Patent number
US03985777

Reaction notes

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