m-Chloroperbenzoic acid → HCID 60207471, compound

HRID 1192251Notes

Reaction equation

HRID 1192251 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:25])[C:7]=1[S:8][C:9]1[S:13][C:12]([C:14]([NH:16][CH2:17][CH2:18][CH2:19][S:20][CH3:21])=[O:15])=[CH:11][C:10]=1[N+:22]([O-:24])=[O:23].C1C=C(Cl)C=C(C(OO)=[O:34])C=1>>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:25])[C:7]=1[S:8][C:9]1[S:13][C:12]([C:14]([NH:16][CH2:17][CH2:18][CH2:19][S:20]([CH3:21])=[O:34])=[O:15])=[CH:11][C:10]=1[N+:22]([O-:24])=[O:23]

Participants

3

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 60207418HCID 60207418, compound

Product 1

HCID 60207471HCID 60207471, compound

Procedure

Prepared according to the procedure described for example 34 from 5-((3,5-dichloropyridin-4-yl)thio)-N-(3-(methylthio)propyl)-4-nitrothiophene-2-carboxamide (100 mg, 0.23 mmol) and MCPBA (198 mg, 1.15 mmol). The titled product was obtained as a white solid (72.0 mg, 69% yield). 1H NMR (400 MHz, d6-DMSO) δ: 8.99 (2H, m), 8.93 (1H, m), 8.41 (1H, s), 3.30 (2H, m), 2.80 (1H, m), 2.64 (1H, m), 2.50 (3H, s), 1.84 (2H, m). MS m/z: 454.08, 456.08 [M+H]+.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-65b0220bfe774e488e501e4e38817da9
Source dataset
uspto-grants-2014_03
Patent number
US08680139B2

Reaction notes

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