Water → HCID 28739719, compound

HRID 1800446Notes

Reaction equation

HRID 1800446 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.O.C(=O)([O-])O.[Na+].[F:15][C:16]([F:27])([F:26])[C:17]1[CH:18]=[C:19]([CH:23]=[CH:24][CH:25]=1)[C:20](Cl)=[O:21]>O1CCCC1>[OH:8][C:4]1[CH:3]=[C:2]([NH:1][C:20](=[O:21])[C:19]2[CH:23]=[CH:24][CH:25]=[C:17]([C:16]([F:15])([F:26])[F:27])[CH:18]=2)[CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 115683-AminophenolHCID 752573-(Trifluoromethyl)benzoyl chlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 28739719HCID 28739719, compoundYield 108.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-aminophenol (11.3 g, 104 mmol) in tetrahydrofuran (250 mL) were added water (250 mL) in which sodium hydrogen carbonate (10.6 g, 126.4 mmol) has been dissolved and 3-(trifluoromethyl)benzoyl chloride (22.4 g, 107 mmol), and the mixture was vigorously stirred at room temperature for 2 hr. The aqueous layer was separated, and the organic layer was diluted with ethyl acetate (150 mL) and washed with saturated brine (150 mL). The combined aqueous layer was extracted with ethyl acetate (150 mL). The combined organic layer was dried over anhydrous magnesium sulfate, the insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The crude product was recrystallized from ethyl acetate and hexane to give title compound (31.7 g) as pale-brown crystals.

Workup

  1. dissolutionhas been dissolved
  2. customThe aqueous layer was separated
  3. additionthe organic layer was diluted with ethyl acetate (150 mL)
  4. washwashed with saturated brine (150 mL)
  5. extractionThe combined aqueous layer was extracted with ethyl acetate (150 mL)
  6. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  7. filtrationthe insoluble material was filtered off
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customThe crude product was recrystallized from ethyl acetate and hexane

Sources & evidence

ORD record
ord-9050ab8a8b554b9bae4a76d5cb521e36
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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