Methanol → 2-Methoxycarbonyl-5-nitrobenzenesulfonic acid

HRID 995

Reaction equation

HRID 995 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:5]=1[S:13]([OH:16])(=[O:15])=[O:14])([OH:3])=[O:2].S(Cl)(Cl)=O.[CH3:21]O>CN(C=O)C>[CH3:21][O:2][C:1]([C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:5]=1[S:13]([OH:16])(=[O:15])=[O:14])=[O:3]

Participants

5

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 4070254-Nitro-2-sulfobenzoic acid

Product 1

HCID 196938012-Methoxycarbonyl-5-nitrobenzenesulfonic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of 190.0 g (0.77 mol) of 2-carboxy-5-nitrobenzenesulfonic acid, 10 ml of DMF and 250 ml (3.43 mol) of thionyl chloride is heated at boiling for 3 h. After separating off the insoluble constituents by filtration, the filtrate is concentrated. 200 ml (4.94 mol) of methanol are added to the residue which results. When addition is complete the reaction mixture is cooled to 0° C. The solid which precipitates is filtered off and dried. 70.9 g (35.3% of theory) of colorless, crystalline 2-methoxycarbonyl-5-nitrobenzenesulfonic acid (m.p.: 92°-94° C.) are thus obtained. By distilling off the volatile components from the mother liquor, a second fraction (62.5 g, 31.1% of theory) is obtained.

Workup

  1. temperatureis heated
  2. customAfter separating off the insoluble constituents
  3. filtrationby filtration
  4. concentrationthe filtrate is concentrated
  5. customresults
  6. additionWhen addition
  7. customThe solid which precipitates
  8. filtrationis filtered off
  9. customdried

Sources & evidence

ORD record
ord-ef5dd0a2d9f54429bb4780c2b3d7888b
Source dataset
uspto-grants-1998_03
Patent number
US05723409

Linked notes

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