Acetanilide → HCID 12798655, compound

HRID 1931265Notes

Reaction equation

CO[CH:3]([O:14]C)[C:4]1[CH:9]=[CH:8][C:7](I)=[C:6]([N+:11]([O-])=O)[CH:5]=1.[C:16]1([NH:22][C:23](=O)[CH3:24])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>>[CH3:24][C:23]1[N:22]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:7]2[CH:8]=[CH:9][C:4]([CH:3]=[O:14])=[CH:5][C:6]=2[N:11]=1

Participants

Reactant 2

HCID 904Acetanilide

HCID 66720019HCID 66720019, compound

Product 1

HCID 12798655HCID 12798655, compoundYield 67%

Procedure

Method A applied to 4-dimethoxymethyl-1-iodo-2-nitrobenzene (155 mg, 0.5 mmol) and N-phenylacetamide (81 mg, 0.6 mmol) yielded the title compound as pale yellow oil (79 mg, 67% yield). 1H NMR (DMSO) δ 2.50 (s, 3H), 7.31 (d, J=8.3Hz, 1H), 7.61-7.68 (m, 5H), 7.82 (d, J=8.3Hz, 1H), 8.25 (s, 1H), 10.10 (s, 1H); 13C NMR δ 13.6, 111.4, 120.1, 124.2, 127.0, 129.8, 130.2, 132.3, 139.1, 154.7, 158.3, 192.4. HRMS (FAB): cal. for C15H13N2O [M+H+]: 237.1028; found: 237.1024.

Sources & evidence

ORD record: ord-0b821fa0a0eb4530bb435656b57e1b9f
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188282B2

Reaction notes

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