Chloroform → HCID 69108697, compound

HRID 1838263Notes

Reaction equation

HRID 1838263 reaction equation
[CH3:1][CH:2]1[CH2:7][N:6]([C:8]([N:10]2[CH2:15][CH2:14][S:13][CH2:12][CH2:11]2)=[O:9])[CH:5]([CH3:16])[CH2:4][N:3]1[C:17]1[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[C:19]([C:25]([F:28])([F:27])[F:26])[CH:18]=1.C(=O)(O)[O-:30].[Na+].ClC1C=CC=C(C(OO)=O)C=1.C(Cl)(Cl)Cl>ClCCl>[CH3:1][C@H:2]1[CH2:7][N:6]([C:8]([N:10]2[CH2:11][CH2:12][S:13](=[O:30])[CH2:14][CH2:15]2)=[O:9])[C@H:5]([CH3:16])[CH2:4][N:3]1[C:17]1[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[C:19]([C:25]([F:27])([F:28])[F:26])[CH:18]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 18753353HCID 18753353, compound

Product 1

HCID 69108697HCID 69108697, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 270 mg portion of 4-[2,5-dimethyl-4-(thiomorpholine-4-carbonyl)piperazin-1-yl]-2-trifluoromethylbenzonitrile synthesized in Example 7-6 was dissolved in 7 ml of dichloromethane, and the solution was mixed with 110 mg of sodium bicarbonate and 155 mg of m-chloroperbenzoic acid (MCPBA) at −78° C. and stirred at the same temperature for 6 hours. The reaction solution was mixed with chloroform, washed with 1 N aqueous sodium hydroxide and saturated brine and then dried over sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by a silica gel column chromatography to obtain 232 mg of the title compound from methanol-chloroform (1:50, v/v) eluate.

Workup

  1. washwashed with 1 N aqueous sodium hydroxide and saturated brine
  2. dry with materialdried over sodium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-ea3c77c0409945b299562d4c30d6c295
Source dataset
uspto-grants-2004_01
Patent number
US06673799B1

Reaction notes

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