Acetanilide → HCID 24821365, compound

HRID 1931261Notes

Reaction equation

HRID 1931261 reaction equation
Cl[C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N+:9]([O-])=O.[C:12]1([NH:18][C:19](=O)[CH3:20])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[Cl:8][C:7]1[C:2]2[N:18]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:19]([CH3:20])=[N:9][C:3]=2[CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 2

HCID 904AcetanilideHCID 185552,3-Dichloronitrobenzene

Product 1

HCID 24821365HCID 24821365, compoundYield 67%

Procedure

Method A applied to 2,3-dichloronitrobenzene (96 mg, 0.5 mmol) and N-phenylacetamide (81 mg, 0.6 mmol) yielded the title compound as a brown solid (81 mg, 67%). mp 103-105° C. 1H NMR (DMSO) δ 2.38 (s, 3H), 7.30-7-33 (m, 2H), 7.56-7.62 (m, 5H), 7.70 (dd, J=5.4, 3.7Hz, 1H); 13C NMR δ 13.2, 115.9, 116.0, 124.5, 125.0, 128.7, 129.3, 130.2, 134.6, 138.9, 153.7, 158.5. HRMS (FAB): cal. for C14H12N2Cl [M+H+]: 243.0689; found: 243.0683.

Sources & evidence

ORD record
ord-ab633fc0caef476888134dc84ce2a428
Source dataset
uspto-grants-2012_05
Patent number
US08188282B2

Reaction notes

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