m-Chloroperbenzoic acid → HCID 22057734, compound

HRID 891261Notes

Reaction equation

HRID 891261 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[N:12]1[CH:17]=[CH:16][C:15]([CH2:18][NH:19][C:20]2[CH:38]=[CH:37][CH:36]=[CH:35][C:21]=2[C:22]([NH:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:34])([F:33])[F:32])[CH:26]=2)=[O:23])=[CH:14][CH:13]=1>ClCCl>[O-:6][N+:12]1[CH:17]=[CH:16][C:15]([CH2:18][NH:19][C:20]2[CH:38]=[CH:37][CH:36]=[CH:35][C:21]=2[C:22]([NH:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:32])([F:33])[F:34])[CH:26]=2)=[O:23])=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 63988832-[(4-Pyridinylmethyl)amino]-N-[3-(trifluoromethyl)phenyl]benzamide

Product 1

HCID 22057734HCID 22057734, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-Chloroperoxybenzoic acid (2.06 g of 70%, 8.4 mmol) is added to a stirred mixture of 2-[(4-pyridyl)methyl]amino-N-[3-(trifluoromethyl)phenyl]benzamide (Example 14; 1.86 g, 5 mmol) in dichloromethane (50 mL) at 0° C. The resulting mixture is then stirred at room temperature for 15 hours. The mixture is diluted with dichloromethane (100 mL) and washed sequentially with aqueous sodium hydroxide (2×100 mL) and aqueous sodium thiosulphate (2×50 mL of 10%). The organic phase is dried (Na2SO4), filtered and the solvent is evaporated off under reduced pressure to yield the crude product which is purified by column chromatography on silica gel, eluent 20% ethanol in ethyl acetate, and recrystallised from ethyl acetate-hexane to give the title compound as a colourless crystalline solid, m.p. 181–184° C.

Workup

  1. washwashed sequentially with aqueous sodium hydroxide (2×100 mL) and aqueous sodium thiosulphate (2×50 mL of 10%)
  2. dry with materialThe organic phase is dried (Na2SO4)
  3. filtrationfiltered
  4. customthe solvent is evaporated off under reduced pressure
  5. customto yield the crude product which
  6. customis purified by column chromatography on silica gel, eluent 20% ethanol in ethyl acetate
  7. customrecrystallised from ethyl acetate-hexane

Sources & evidence

ORD record
ord-cc26beea760f45f98455040181ffbabc
Source dataset
uspto-grants-2006_02
Patent number
US07002022B2

Reaction notes

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