Methanol → Methyl 3-nitro-4-phenoxy-5-sulfamoylbenzoate

HRID 596310Notes

Reaction equation

HRID 596310 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([S:20](=[O:23])(=[O:22])[NH2:21])[C:12]=1[O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:7]([OH:9])=[O:8])([O-:3])=[O:2].OS(O)(=O)=O.[CH3:29]O>>[CH3:29][O:8][C:7](=[O:9])[C:6]1[CH:10]=[C:11]([S:20](=[O:23])(=[O:22])[NH2:21])[C:12]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 1199263-(Aminosulfonyl)-5-nitro-4-phenoxybenzoic acid

Product 1

HCID 53854447Methyl 3-nitro-4-phenoxy-5-sulfamoylbenzoate

Procedure

34 g (~0.1 mol) of 3-nitro-4-phenoxy-5-sulphamylbenzoic acid are dissolved in 150 ml of methanol and are heated to the boil. 5.4 ml of concentrated H2SO4 are then added slowly dropwise and the mixture is heated at reflux temperature for 10 hours. On cooling, 3-nitro-4-phenoxy-5-sulphamylbenzoic acid methyl ester crystallises.

Workup

  1. temperatureare heated to the boil
  2. temperaturethe mixture is heated
  3. temperatureat reflux temperature for 10 hours
  4. temperatureOn cooling
  5. custom3-nitro-4-phenoxy-5-sulphamylbenzoic acid methyl ester crystallises

Sources & evidence

ORD record
ord-1248ada3f3ac430da5e68e11ecc5a4a9
Source dataset
uspto-grants-1977_03
Patent number
US04010273

Reaction notes

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