Ethyl orthoformate → HCID 118035693, compound

HRID 1750062Notes

Reaction equation

HRID 1750062 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([S:8][C:9]([F:12])([F:11])[F:10])[CH:5]=[CH:4][C:3]=1[OH:13].[CH:14](OCC)(OCC)OCC.C(=O)(O)[O-].[Na+]>>[F:11][C:9]([S:8][C:6]1[CH:5]=[CH:4][C:3]2[O:13][CH:14]=[N:1][C:2]=2[CH:7]=1)([F:12])[F:10]

Participants

4

Reactant 3

HCID 31214Ethyl orthoformateHCID 516892Sodium BicarbonateHCID 230231052-Amino-4-[(trifluoromethyl)thio]phenol

Product 1

HCID 118035693HCID 118035693, compound

Procedure

A mixture of 0.50 g of 2-amino-4-trifluoromethylsulfanylphenol and 3 ml of triethyl orthoformate was stirred under heating and refluxing for 3 hours. A saturated aqueous sodium bicarbonate solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was applied to a silica gel column chromatography to obtain 0.50 g of 5-trifluoromethylsulfanylbenzoxazole.

Workup

  1. temperatureunder heating
  2. temperaturerefluxing for 3 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6d15edbfc8ea4f59b99d76745f821035
Source dataset
uspto-grants-2015_10
Patent number
US09156838B2

Reaction notes

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