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

HRID 1763381Notes

Reaction equation

HRID 1763381 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-7daf1b8c5c2c4ef7a0c7d924767b14ec
Source dataset
uspto-grants-1978_09
Patent number
US04111953

Reaction notes

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