m-Chloroperbenzoic acid → HCID 54671266, compound

HRID 449309Notes

Reaction equation

HRID 449309 reaction equation
[Cl:1][C:2]1[CH:12]=[C:11]([C:13]2[N:18]=[C:17]3[N:19]([CH2:22][C:23]4[CH:24]=[C:25]5[C:30](=[CH:31][CH:32]=4)[N:29]=[CH:28][CH:27]=[CH:26]5)[N:20]=[N:21][C:16]3=[CH:15][CH:14]=2)[CH:10]=[CH:9][C:3]=1[C:4]([NH:6]CC)=[O:5].ClC1C=CC=C(C(OO)=[O:41])C=1>ClCCl.O>[C:4]([C:3]1[CH:9]=[CH:10][C:11]([C:13]2[N:18]=[C:17]3[N:19]([CH2:22][C:23]4[CH:24]=[C:25]5[C:30](=[CH:31][CH:32]=4)[N+:29]([O-:41])=[CH:28][CH:27]=[CH:26]5)[N:20]=[N:21][C:16]3=[CH:15][CH:14]=2)=[CH:12][C:2]=1[Cl:1])(=[O:5])[NH2:6]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 58514638HCID 58514638, compound

Product 1

HCID 54671266HCID 54671266, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of example 119 (0.060 g, 0.135 mmol) in dichloromethane (1 ml), 3-chloroperbenzoic acid (0.46 g, 0.270 mmol) was added and stirred at RT for 12 h. The mixture was diluted with water, extracted with dichloromethane, the organic layer dried over sodium sulphate and concentrated. The crude product was purified by column chromatography with methanol:dichloromethane as the eluent to afford the title compound as a grey solid. (0.016 g, 26%). M.P.: 212-215° C. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 8.71 (d, J=8.8 Hz, 1H), 8.68 (d, J=9.1 Hz, 1H), 8.56 (m, 2H), 8.30 (d, J=1.5 Hz, 1H), 8.24 (m, 2H), 8.12 (s, 1H), 7.93 (d, J=8.6 Hz, 1H), 7.86 (dd, J=9.1, 1.8 Hz, 1H), 7.57 (d, J=8.0 Hz, 1H), 7.48 (dd, J=8.4, 6.0 Hz, 1H), 6.20 (s, 2H), 3.28 (m, 2H), 1.14 (t, J=7.3 Hz, 3H).

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialthe organic layer dried over sodium sulphate
  3. concentrationconcentrated
  4. customThe crude product was purified by column chromatography with methanol

Sources & evidence

ORD record
ord-0dd307288574472ca4214b4fff5a37da
Source dataset
uspto-grants-2013_07
Patent number
US08481739B2

Reaction notes

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