Hydrochloric Acid → HCID 15480132, compound

HRID 1872776Notes

Reaction equation

HRID 1872776 reaction equation
[NH2:1][C:2]1[C:7]([CH3:8])=[C:6]([NH:9][C:10](=[O:15])[C:11]([F:14])([F:13])[F:12])[CH:5]=[CH:4][C:3]=1[OH:16].Cl.[CH:18](OCC)(OCC)OCC>CO>[CH3:8][C:7]1[C:2]2[N:1]=[CH:18][O:16][C:3]=2[CH:4]=[CH:5][C:6]=1[NH:9][C:10](=[O:15])[C:11]([F:12])([F:13])[F:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 31214Ethyl orthoformateHCID 15480131HCID 15480131, compound

Product 1

HCID 15480132HCID 15480132, compoundYield 76.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 2-amino-3-methyl-4-trifluoroacetamidophenol (4.25 g, 18.15 mmol) and concentrated hydrochloric acid (45 mL) in methanol (5.2 mL) is treated with triethyl orthoformate (2.98 mL, 27.2 mmol). A simple distillation apparatus is attached and the mixture is heated with an oil bath to 90° C. and methanol is distilled from the reaction. The reaction mixture is cooled to room temperature and distributed between ethyl ether (200 mL) and water (20 mL). The ether layer is washed with a 0.1 M aqueous solution of sodium hydroxide (20 mL), dried over magnesium sulfate and concentrated under reduced pressure to yield 3.40 g of 4-methyl-5-trifluoroacetamidobenzoxazole as an orange solid.

Workup

  1. distillationA simple distillation apparatus
  2. distillationmethanol is distilled from the reaction
  3. temperatureThe reaction mixture is cooled to room temperature
  4. washThe ether layer is washed with a 0.1 M aqueous solution of sodium hydroxide (20 mL)
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4997f595bc4644dda70fc36975ce2f09
Source dataset
uspto-grants-2000_08
Patent number
US06110952

Reaction notes

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