2-(2-Trifluoromethyl-thiazol-4-yl)ethylene oxide → N-[2-(4-Carbomethoxyphenyl)-1-methylethyl]-2-hydroxy-2-(2-trifluoromethyl-thiazol-4-yl)ethanamine

HRID 477158Notes

Reaction equation

HRID 477158 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[S:4][CH:5]=[C:6]([CH:8]2[O:10][CH2:9]2)[N:7]=1.[C:13]([C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH:24]([NH2:26])[CH3:25])=[CH:19][CH:18]=1)([O:15][CH3:16])=[O:14]>C(O)C>[C:13]([C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH:24]([NH:26][CH2:9][CH:8]([OH:10])[C:6]2[N:7]=[C:3]([C:2]([F:12])([F:11])[F:1])[S:4][CH:5]=2)[CH3:25])=[CH:19][CH:18]=1)([O:15][CH3:16])=[O:14]

Participants

4

Reactant 2

HCID 143728612-(2-Trifluoromethyl-thiazol-4-yl)ethylene oxideHCID 15034329Methyl 4-(2-aminopropyl)benzoate

Product 1

HCID 19974173N-[2-(4-Carbomethoxyphenyl)-1-methylethyl]-2-hydroxy-2-(2-trifluoromethyl-thiazol-4-yl)ethanamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

0.54 g (0.030 mol) of 2-(2-trifluoromethyl-thiazol-4-yl)ethylene oxide is dissolved in 5 ml of ethanol, and the solution is added dropwise within 10 minutes to a boiling solution of 0.58 g (0.0030 mol) of 2-(4-carbomethoxyphenyl)-1-methylethylamine in 13 ml ethanol. The mixture is then boiled under reflux for 5 hours, the solvent is removed by distillation, and the base is purified on a silica gel column using methylene chloride/methanol=20:1 as eluant.

Workup

  1. temperatureunder reflux for 5 hours
  2. customthe solvent is removed by distillation
  3. customthe base is purified on a silica gel column

Sources & evidence

ORD record
ord-7144da5320a74224990d241e06098fcd
Source dataset
uspto-grants-1989_12
Patent number
US04886814

Reaction notes

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