4-Methoxyphenol → 4-(p-Methoxyphenoxy)-3-nitro-5-sulphamyl-benzoic acid

HRID 1287715Notes

Reaction equation

HRID 1287715 reaction equation
Cl[C:2]1[C:10]([S:11](=[O:14])(=[O:13])[NH2:12])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:15]([O-:17])=[O:16].[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1>C(=O)(O)[O-].[Na+]>[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][C:2]2[C:10]([S:11](=[O:14])(=[O:13])[NH2:12])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=2[N+:15]([O-:17])=[O:16])=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 90154-MethoxyphenolHCID 898934-Chloro-3-nitro-5-sulphamoylbenzoic acid

Product 1

HCID 213120984-(p-Methoxyphenoxy)-3-nitro-5-sulphamyl-benzoic acid

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 4-chloro-3-nitro-5-sulphamyl-benzoic acid (14 g), p-methoxyphenol (9.3 g), and 1N sodium bicarbonate (200 ml) was stirred at 90° C for 5 hours. After cooling, the resulting 4-(p-methoxyphenoxy)-3-nitro-5-sulphamyl-benzoic acid was precipitated by the addition of 4N hydrochloric acid until the pH was 1, and collected by suction. The crude acid was dissolved in hot methanol (100 ml) and precipitated by the addition of water (100 ml) and cooling. After collection and drying in vacuo, the melting point was 229°-230° C.

Workup

  1. temperatureAfter cooling
  2. customthe resulting 4-(p-methoxyphenoxy)-3-nitro-5-sulphamyl-benzoic acid was precipitated by the addition of 4N hydrochloric acid until the pH was 1
  3. customcollected by suction
  4. dissolutionThe crude acid was dissolved in hot methanol (100 ml)
  5. customprecipitated by the addition of water (100 ml)
  6. temperaturecooling
  7. customAfter collection
  8. customdrying in vacuo

Sources & evidence

ORD record
ord-294a22f097ca4feca4a3074e07fddf4f
Source dataset
uspto-grants-1976_10
Patent number
US03985777

Reaction notes

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