Sulfuric Acid → HCID 19862783, compound

HRID 1165266Notes

Reaction equation

HRID 1165266 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]([N+:13]([O-])=O)[CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7])([O-])=O.S(=O)(=O)(O)O.[CH2:21](O)[CH:22]([CH3:24])[CH3:23]>C1(C)C=CC=CC=1>[CH2:21]([O:8][C:6](=[O:7])[C:5]1[CH:9]=[CH:10][C:11]([NH2:13])=[CH:12][C:4]=1[NH2:1])[CH:22]([CH3:24])[CH3:23]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 6560IsobutanolHCID 118802,4-Dinitrobenzoic acid

Product 1

HCID 19862783HCID 19862783, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of 212 g of 2,4-dinitrobenzoic acid in 300 ml of toluene were added 38 g of concentrated sulfuric acid and 230 ml of isobutyl alcohol. The mixture was refluxed for 10 hrs and the resulting water removed by azeotropic distillation. After this period the mixture was cooled to room temperature and washed with 1000 ml of an aqueous 5% NaHCO3 solution followed by two 500 ml water washings. The toluene was removed at reduced pressure and the resulting dark oil was washed with hexane to yield 252 g of isobutyl-2,4-diaminobenzoate, a fluffy white crystalline solid, mp 54°-55° C.

Workup

  1. temperatureThe mixture was refluxed for 10 hrs
  2. customthe resulting water removed by azeotropic distillation
  3. washwashed with 1000 ml of an aqueous 5% NaHCO3 solution
  4. customThe toluene was removed at reduced pressure
  5. washthe resulting dark oil was washed with hexane

Sources & evidence

ORD record
ord-4bb07c2d2cba4777a3e3b04ae597dc58
Source dataset
uspto-grants-1990_03
Patent number
US04908394

Reaction notes

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