Acetic Acid → HCID 66906147, compound

HRID 1692180Notes

Reaction equation

HRID 1692180 reaction equation
[CH2:1]([O:3][C:4]([NH:6][C:7]1[C:15]([CH3:16])=[CH:14][CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=[O:10])=[O:5])[CH3:2].C(O)(=O)C.[ClH:21].OO>O>[Cl:21][C:13]1[CH:14]=[C:15]([CH3:16])[C:7]([NH:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])=[C:8]([CH:12]=1)[C:9]([OH:11])=[O:10]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 28156973HCID 28156973, compound

Product 1

HCID 66906147HCID 66906147, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
37.5 °C

Procedure

A 2-L reactor equipped with overhead stirrer and thermocouple was charged with 150 g (0.672 mol) of 2-[(ethoxycarbonyl)amino]-3-methylbenzoic acid (ca. 98% purity) and acetic acid (500 g). The resulting slurry was heated to 35-40° C. to give a solution, which was cooled to 30° C., and then hydrochloric acid (37%, 150 g, 1.5 mol, 2.2 eq) was added. The mixture was maintained at 30° C. while aqueous hydrogen peroxide (30%, 96 g, 0.85 mol, 1.25 eq) was added over about 1 h. The mixture was then warmed to 35° C. and held at that temperature for about 1 h. About 600 mL of water was metered in over about 30 minutes, while maintaining the temperature at 30-35° C. The mixture was cooled to 10° C., and the product was collected by filtration, and the wet cake was washed with water (3×100 mL); the third wash tested negative with KI-starch paper. The wet cake was dried to constant weight in a vacuum oven at 50° C. The crude yield was about 150 g (about 84% based on an estimated purity of 2-[(ethoxycarbonyl)amino]-3-methylbenzoic acid of 98% and estimated product purity of 95%). A portion of the crude product was first recrystallized from toluene and then recrystallized from aqueous methanol to give an analytical sample melting at 124-126° C.

Workup

  1. customA 2-L reactor equipped with overhead stirrer
  2. customto give a solution, which
  3. temperaturewas cooled to 30° C.
  4. additionwas added over about 1 h
  5. temperatureThe mixture was then warmed to 35° C.
  6. customwas metered in over about 30 minutes
  7. temperaturewhile maintaining the temperature at 30-35° C
  8. temperatureThe mixture was cooled to 10° C.
  9. filtrationthe product was collected by filtration
  10. washthe wet cake was washed with water (3×100 mL)
  11. washthe third wash
  12. customThe wet cake was dried to constant weight in a vacuum oven at 50° C
  13. customA portion of the crude product was first recrystallized from toluene
  14. customrecrystallized from aqueous methanol
  15. customto give an analytical sample melting at 124-126° C.

Sources & evidence

ORD record
ord-0d63b1cd52c847379f4916ae14c46044
Source dataset
uspto-grants-2012_04
Patent number
US08153844B2

Reaction notes

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