Acetyl chloride → HCID 69203994, compound

HRID 2378220Notes

Reaction equation

HRID 2378220 reaction equation
[C:1]([CH:3]=[C:4]([C:15]1[CH:16]=[CH:17][C:18]([O:25][CH3:26])=[C:19]([NH:21][C:22](=[O:24])[CH3:23])[CH:20]=1)[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([O:13][CH3:14])[CH:6]=1)#[N:2].N[C:28]1C=C(C(C2C=CC(OC)=C(OCC)C=2)=CC#N)C=CC=1OC.C(Cl)(=O)C>CCCCCC>[C:1]([CH:3]=[C:4]([C:15]1[CH:16]=[CH:17][C:18]([O:25][CH3:26])=[C:19]([NH:21][C:22](=[O:24])[CH3:23])[CH:20]=1)[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([O:13][CH2:14][CH3:28])[CH:6]=1)#[N:2]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 69204282HCID 69204282, compoundHCID 69204885HCID 69204885, compound

Product 1

HCID 69203994HCID 69203994, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

N-{5-[2-Cyano-1-(3-ethoxy-4-methoxy-phenyl)-vinyl]-2-methoxy-phenyl}-acetamide (E and Z isomers) were prepared analogously to N-{5-[2-cyano-1-(3,4-dimethoxy-phenyl)-vinyl]-2-methoxy-phenyl}-acetamide using 3-(3-amino-4-methoxy-phenyl)-3-(3-ethoxy-4-methoxy-phenyl)-acrylonitrile (0.4 g, 1.1 mmol) and acetyl chloride (1.1 mL). The crude product was slurried with hexane to give N-{5-[2-cyano-1-(3-ethoxy-4-methoxy-phenyl)-vinyl]-2-methoxy-phenyl}-acetamide (0.2 g, 41%) as a white solid: mp 155-157° C.; 1H NMR (CDCl3) δ 9.25 (d, J=2 Hz, 1H), 7.90 (d, 13.5 Hz, 1H), 7.17-6.90 (m, 3H), 6.75 (d, J=1 Hz, 1H), 6.13 (s, 1H), 5.97 (s, 1H), 4.02-3.97 (m, 2H), 3.94-3.97 (m, 6H), 2.07 (d, J=7 Hz, 3H), 1.70 (t, 3H); 13C NMR (CDCl3) δ 161.29, 151.18, 150.02, 147.76, 147.32, 130.47, 130.23, 129.18, 128.91, 127.26, 127.22, 122.40, 122.18, 118.77, 118.70, 113.81, 122.20, 111.43, 111.34, 111.04, 110.77, 92.73, 92.45, 63.76, 63.71, 55.87, 55.41, 23.80, 23.68, 14.57; Anal Calcd for C21H22N2O4: C, 68.84; H, 6.05; N, 7.65. Found: C, 68.94, 5.93; N, 7.53.

Sources & evidence

ORD record
ord-1ea2089cc820407ca7971951bf44692c
Source dataset
uspto-grants-2008_12
Patent number
US07470723B2

Reaction notes

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