m-Chloroperbenzoic acid → HCID 44217833, compound

HRID 1669706Notes

Reaction equation

HRID 1669706 reaction equation
[CH3:1][C:2]1[O:6][C:5]([CH2:7][NH:8][C:9]2[CH:18]=[CH:17][C:16]3[C:15]([NH:19][CH2:20][CH2:21][S:22][CH3:23])=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=2)=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:32])C=1>ClCCl>[CH3:23][S:22]([CH2:21][CH2:20][NH:19][C:15]1[C:16]2[CH:17]=[CH:18][C:9]([NH:8][CH2:7][C:5]3[O:6][C:2]([CH3:1])=[CH:3][CH:4]=3)=[N:10][C:11]=2[CH:12]=[CH:13][CH:14]=1)=[O:32]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 44217832HCID 44217832, compound

Product 1

HCID 44217833HCID 44217833, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N2-(5-Methyl-furan-2-ylmethyl)-N5-(2-methylsulfanyl-ethyl)-quinoline-2,5-diamine (200 mg, 0.61 mmol) were dissolved in 6.5 mL dichloromethane and meta-chloro-perbenzoic acid was added (220 mg, 1.3 mmol). The reaction mixture was stirred at room temperature overnight. The reaction mixture was quenched by addition of 10 mL water and 10 mL 2N sodium carbonate solution. The mixture was extracted three times with ethyl acetate (50 mL each). The organic phases ware pooled, dried with sodium sulfate, filtered and evaporated. The reaction mixture was purified by flash chromatography on silica gel (dichloromethane/methanol 100:0→90:10 gradient). The title compound was obtained as a white solid (60 mg, 29%), MS: m/e=344.3 (M+H+) together with N5-(2-methanesulfonyl-ethyl)-N2-(5-methyl-furan-2-ylmethyl)-quinoline-2,5-diamine.

Workup

  1. customThe reaction mixture was quenched by addition of 10 mL water and 10 mL 2N sodium carbonate solution
  2. extractionThe mixture was extracted three times with ethyl acetate (50 mL each)
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe reaction mixture was purified by flash chromatography on silica gel (dichloromethane/methanol 100:0→90:10 gradient)

Sources & evidence

ORD record
ord-63d98e5e02b64345811e44c708cd7698
Source dataset
uspto-grants-2011_08
Patent number
US07989628B2

Reaction notes

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