Dimethyl Sulfoxide → HCID 86743551, compound

HRID 476769Notes

Reaction equation

HRID 476769 reaction equation
[F:1][C:2]1[C:7](F)=[C:6]([F:9])[C:5]([F:10])=[C:4]([C:11]([O:13][CH3:14])=[O:12])[C:3]=1[C:15]([O:17][CH3:18])=[O:16].CS(C)=O.[C:23]([NH2:28])([CH2:26][CH3:27])([CH3:25])[CH3:24]>O>[CH3:24][C:23]([NH:28][C:7]1[C:2]([F:1])=[C:3]([C:15]([O:17][CH3:18])=[O:16])[C:4]([C:11]([O:13][CH3:14])=[O:12])=[C:5]([F:10])[C:6]=1[F:9])([CH3:25])[CH2:26][CH3:27]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 689862-Butanamine, 2-methyl-HCID 616675dimethyl tetrafluorophthalate

Product 1

HCID 86743551HCID 86743551, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3,4,5,6-Tetrafluoro-1,2-benzenedicarboxylic acid, dimethyl ester (Example 1), 2.66 g, is treated with 8 g of dimethylsulfoxide and the mixture is warmed to dissolve the solid. The solution is cooled in an ice bath and 2.65 g of tertiary-pentylamine is added. The resulting solution is then stirred at room temperature for three hours, 50 ml of water added, and the solution extracted with heptanes (2×30 ml). The combined heptane extract is extracted with a 5% aqueous solution of hydrochloric acid (2×4 ml) and concentrated to give 4-[(1,1-dimethylpropyl)amino]-3,5,6-trifluoro-1,2-benzenedicarboxylic acid, dimethyl ester as an oil. Hydrochloric acid (36% aqueous solution), 20 ml, is added to this oil and the resulting mixture is heated at reflux for 20 hours. The solution is concentrated to 4-5 ml and then diluted with water (20 ml). Cooling gave crystals which are collected and vacuum dried to give 1.2 g of 3-amino-2,4,5-trifluorobenzoic acid (63%); mp 133° -136° C.; GC (97.9%); HPLC (94%).

Workup

  1. temperaturethe mixture is warmed
  2. dissolutionto dissolve the solid
  3. temperatureThe solution is cooled in an ice bath
  4. extractionthe solution extracted with heptanes (2×30 ml)
  5. extractionThe combined heptane extract
  6. extractionis extracted with a 5% aqueous solution of hydrochloric acid (2×4 ml)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-fb642c51183e405c8b98af896c6a7963
Source dataset
uspto-grants-1989_12
Patent number
US04885386

Reaction notes

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