Acetanilide → HCID 11229794, compound

HRID 1931262Notes

Reaction equation

HRID 1931262 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:11].[C:12]1([NH:18][C:19](=O)[CH3:20])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[CH3:20][C:19]1[N:18]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:2]2[C:3]([CH3:11])=[CH:4][CH:5]=[CH:6][C:7]=2[N:8]=1

Participants

3

Reactant 2

HCID 904AcetanilideHCID 775912-Chloro-3-nitrotoluene

Product 1

HCID 11229794HCID 11229794, compound

Procedure

Method A applied to 2-chloro-3-nitrotoluene (68 mg, 0.5 mmol) and N-phenylacetamide (81 mg, 0.6 mmol) yielded the title compound as a pale yellow solid. mp 107-109° C. 1H NMR (DMSO) δ 1.83 (s, 3H), 2.34 (s, 3H), 7.02 (d, J=7.8Hz, 1H), 7.22 (t, J=7.8 Hz, 1H), 7.53 (d, J=7.8Hz, 1H), 7.55-7.63 (m, 5H); 13C NMR δ 13.3, 17.1, 114.8, 121.7, 123.0, 125.5, 128.6, 129.4, 129.9, 136.0, 144.5, 151.2, 157.2. HRMS (FAB): cal. for C15H15N2 [M+H+]: 223.1235; found: 223.1231.

Sources & evidence

ORD record
ord-a79f050752a6408389563bc669c7655f
Source dataset
uspto-grants-2012_05
Patent number
US08188282B2

Reaction notes

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