Sodium Hydroxide → HCID 21506100, compound

HRID 1287791Notes

Reaction equation

HRID 1287791 reaction equation
[CH2:1]([NH:8][C:9]1[CH:10]=[C:11]([CH:15]=[C:16]([S:33](=[O:36])(=[O:35])[NH2:34])[C:17]=1[O:18][C:19]1[CH:24]=[CH:23][C:22]([O:25]CC2C=CC=CC=2)=[CH:21][CH:20]=1)[C:12]([OH:14])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[H][H]>O>[CH2:1]([NH:8][C:9]1[CH:10]=[C:11]([CH:15]=[C:16]([S:33](=[O:36])(=[O:35])[NH2:34])[C:17]=1[O:18][C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=1)[C:12]([OH:14])=[O:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21506050HCID 21506050, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 21506100HCID 21506100, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of 3-benzylamino-4-(4-benzyloxyphenoxy)-5-sulphamyl-benzoic acid (0.5 g) in water (5 ml) was adjusted to a pH of 11 by addition of 1N sodium hydroxide. The resulting solution was hydrogenated at room temperature and 1.1 atmospheres hydrogen pressue after addition of Pd-on-carbon powder catalyst (0.025 g catalyst containing 10% of Pd). After the hydrogen uptake had become negligible, the catalyst was removed by filtration, and from the filtrate the 3-benzylamino-4-(4-hydroxyphenoxy)-5-sulphamyl-benzoic acid was precipitated by addition of 4N hydrochloric acid until a pH of 2. After isolation by filtration and recrystallization from aqueous ethanol, the compound was obtained with a melting point of 276°-277° C (decomp.).

Workup

  1. customwas hydrogenated at room temperature
  2. customthe catalyst was removed by filtration
  3. customfrom the filtrate the 3-benzylamino-4-(4-hydroxyphenoxy)-5-sulphamyl-benzoic acid was precipitated by addition of 4N hydrochloric acid until a pH of 2
  4. filtrationAfter isolation by filtration and recrystallization from aqueous ethanol
  5. customthe compound was obtained with a melting point of 276°-277° C (decomp.)

Sources & evidence

ORD record
ord-86f7e9a805044fae91b85e918fae2f64
Source dataset
uspto-grants-1976_10
Patent number
US03985777

Reaction notes

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