Water → 2-m-Cyanophenyl-3-(3-trifluoromethyl-4-chlorophenyl)-5-ethyl oxazolidine

HRID 4123

Reaction equation

HRID 4123 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=[O:7])#[N:2].[F:11][C:12]([F:27])([F:26])[C:13]1[CH:14]=[C:15]([NH:20][CH2:21][CH:22](O)[CH2:23][CH3:24])[CH:16]=[CH:17][C:18]=1[Cl:19].O>C1(C)C=CC=CC=1.CS(O)(=O)=O>[C:1]([C:3]1[CH:4]=[C:5]([CH:6]2[N:20]([C:15]3[CH:16]=[CH:17][C:18]([Cl:19])=[C:13]([C:12]([F:27])([F:11])[F:26])[CH:14]=3)[CH2:21][CH:22]([CH2:23][CH3:24])[O:7]2)[CH:8]=[CH:9][CH:10]=1)#[N:2]

Participants

6

Reactant 3

HCID 962WaterHCID 90670m-FormylbenzonitrileHCID 201526721-(3-Trifluoromethyl-4-chlorophenylamino)-2-butanol

Product 1

HCID 140722002-m-Cyanophenyl-3-(3-trifluoromethyl-4-chlorophenyl)-5-ethyl oxazolidine

Reagents, catalysts & solvents 2

HCID 6395Methanesulfonic AcidCatalystHCID 1140TolueneSolvent

Procedure

Meta-cyanobenzaldehyde (2.1 g, 0.016 mole) was added to 4.3 g of 1-(3-trifluoromethyl-4-chlorophenylamino)-2-butanol in 50 ml of toluene and 2-3 drops of methane sulfonic acid was added. The mixture was refluxed under a modified Dean-Stark apparatus until no more water came off and the mixture was stripped on a rotary evaporator. Yield was 6 g of product, nD30 1.5774. It was characterized by IR and NMR.

Workup

  1. additionwas added
  2. customthe mixture was stripped on a rotary evaporator

Sources & evidence

ORD record
ord-95fce6ee0fd6497e86db89788ce9af11
Source dataset
uspto-grants-1988_02
Patent number
US04723986

Linked notes

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