Water → HCID 19707995, compound

HRID 724781Notes

Reaction equation

HRID 724781 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][O:5][C:3]1=O.[F:8][C:9]([F:19])([F:18])[O:10][C:11]1[CH:12]=[C:13]([CH:15]=[CH:16][CH:17]=1)[NH2:14].C(OCC)C.O>C(OCC)C.CCCCCC>[F:8][C:9]([F:18])([F:19])[O:10][C:11]1[CH:12]=[C:13]([N:14]2[CH2:6][CH2:7][CH:2]([OH:1])[C:3]2=[O:5])[CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 737533-(Trifluoromethoxy)anilineHCID 545831alpha-Hydroxy-gamma-butyrolactone

Product 1

HCID 19707995HCID 19707995, compoundYield 69.3%

Reagents, catalysts & solvents 1

HCID 21584099Diethylether hexaneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of alpha-hydroxy-gamma-butyrolactone (22.0 g) and 3-trifluoromethoxy aniline (19.0 g) was heated to 150° C. (bath temperature) for 48 hours. The mixture was allowed to cool and poured into a mixture of diethyl ether and water. After shaking, the ether layer was separated and the aqueous layer extracted with diethyl ether (x2). The combined ether extracts were washed with 2M hydrochloric acid, water and brine, then dried (MgSO4). The mixture was evaporated under reduced pressure to leave an oil, which on trituration with a mixture of diethyl ether/hexane gave the sub-title compound as an off-white solid (19.42 g).

Workup

  1. temperatureto cool
  2. customthe ether layer was separated
  3. extractionthe aqueous layer extracted with diethyl ether (x2)
  4. washThe combined ether extracts were washed with 2M hydrochloric acid, water and brine
  5. dry with materialdried (MgSO4)
  6. customThe mixture was evaporated under reduced pressure
  7. customto leave an oil, which on trituration

Sources & evidence

ORD record
ord-8b794cb844c44ec19c345030cd8e633f
Source dataset
uspto-grants-1998_01
Patent number
US05705456

Reaction notes

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