3-(Trifluoromethoxy)aniline → HCID 21475353, compound

HRID 2294636Notes

Reaction equation

HRID 2294636 reaction equation
[CH2:1]([O:8][CH:9]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:10]([OH:12])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:21][C:22]([F:32])([F:31])[O:23][C:24]1[CH:25]=[C:26]([CH:28]=[CH:29][CH:30]=1)[NH2:27]>C(OCC)C>[CH2:14]([O:13][CH:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:10]([NH:27][C:26]1[CH:28]=[CH:29][CH:30]=[C:24]([O:23][C:22]([F:21])([F:31])[F:32])[CH:25]=1)=[O:12])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 737533-(Trifluoromethoxy)anilineHCID 12762576HCID 12762576, compound

Product 1

HCID 21475353HCID 21475353, compoundYield 27.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

A solution of dibenzyloxyacetic acid (23.1 g) in diethyl ether (200 ml) was added to a solution of 3-trifluoromethoxyaniline (15 g) in diethyl ether (100 ml). A solution of dicyclohexyldicarbodiimide (16.5 g) in diethyl ether (100 ml) was then added in two portions. The mixture was left overnight and the precipitated solid then filtered off and the filtrate diluted with a mixture of diethyl ether and hexane (5:95) and refrigerated for an hour. The solid which separated was collected and washed with hexane, giving the title compound (10 g) with a melting point of 75°-77° C.

Workup

  1. filtrationthe precipitated solid then filtered off
  2. additionthe filtrate diluted with a mixture of diethyl ether and hexane (5:95) and refrigerated for an hour
  3. customThe solid which separated
  4. customwas collected
  5. washwashed with hexane

Sources & evidence

ORD record
ord-d68fb143a6e0450fb76fa9b6c129af4c
Source dataset
uspto-grants-1997_11
Patent number
US05688962

Reaction notes

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