m-Chloroperbenzoic acid → HCID 54670977, compound

HRID 449286Notes

Reaction equation

HRID 449286 reaction equation
[CH:1]1([NH:4][C:5](=[O:33])[C:6]2[CH:11]=[CH:10][C:9]([C:12]3[N:17]=[C:16]4[N:18]([CH2:21][C:22]5[CH:23]=[C:24]6[C:29](=[CH:30][CH:31]=5)[N:28]=[CH:27][CH:26]=[CH:25]6)[N:19]=[N:20][C:15]4=[CH:14][CH:13]=3)=[CH:8][C:7]=2[F:32])[CH2:3][CH2:2]1.ClC1C=CC=C(C(OO)=[O:42])C=1>ClCCl>[CH:1]1([NH:4][C:5]([C:6]2[CH:11]=[CH:10][C:9]([C:12]3[N:17]=[C:16]4[N:18]([CH2:21][C:22]5[CH:23]=[C:24]6[C:29](=[CH:30][CH:31]=5)[N+:28]([O-:42])=[CH:27][CH:26]=[CH:25]6)[N:19]=[N:20][C:15]4=[CH:14][CH:13]=3)=[CH:8][C:7]=2[F:32])=[O:33])[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 54670422HCID 54670422, compound

Product 1

HCID 54670977HCID 54670977, compoundYield 30.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of example 46 (0.080 g, 0.182 mmol) in dichloromethane (1 ml), m-chloroperbenzoic acid (0.044 g, 0.255 mmol) was added and stirred at RT for 12 h. The reaction mixture was quenched with sodium sulphite solution, washed with saturated potassium carbonate solution and concentrated. The crude product was chromatographed using methanol:dichloromethane to afford the title compound as a pale yellow solid (0.025 g, 30%). M.P.: 89-92° C. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 8.88 (dd, J=4.1, 1.6 Hz, 1H), 8.75 (d, J=9.0 Hz, 1H), 8.51 (m, 2H), 8.28 (t, J=8.1 Hz, 1H), 7.98-7.86 (m, 5H), 7.71 (d, J=8.5 Hz, 1H), 7.32 (dd, J=8.5, 6.1 Hz, 1H), 6.89 (d, J=11.8 Hz, 1H), 6.15 (s, 2H), 2.99 (m, 1H), 0.94 (m, 2H), 0.69 (m, 2H).

Workup

  1. customThe reaction mixture was quenched with sodium sulphite solution
  2. washwashed with saturated potassium carbonate solution
  3. concentrationconcentrated
  4. customThe crude product was chromatographed

Sources & evidence

ORD record
ord-91a4c3d0bd6c47fe81ce32cccedb6d5b
Source dataset
uspto-grants-2013_07
Patent number
US08481739B2

Reaction notes

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