Dimethylformamide dimethyl acetal → N-[[2-chloro-5-[3-(dimethylamino)-1-oxo-2-propen-1-yl]-phenyl]methyl]acetamide

HRID 1408419Notes

Reaction equation

[C:1]([C:4]1[CH:5]=[CH:6][C:7]([Cl:15])=[C:8]([CH2:10][NH:11][C:12](=[O:14])[CH3:13])[CH:9]=1)(=[O:3])[CH3:2].CO[CH:18](OC)[N:19]([CH3:21])[CH3:20]>C1(C)C=CC=CC=1>[Cl:15][C:7]1[CH:6]=[CH:5][C:4]([C:1](=[O:3])[CH:2]=[CH:18][N:19]([CH3:21])[CH3:20])=[CH:9][C:8]=1[CH2:10][NH:11][C:12](=[O:14])[CH3:13]

Participants

Conditions

Temperature: 105 °C

Procedure

A mixture of N-[(5-acetyl-2-chlorophenyl)methyl]acetamide (13.0 g, 57.8 mmol; prepared according to a procedure described in EP 1586552-A1) and N,N-dimethylformamide dimethyl acetal (13.8 g, 115.8 mmol) in toluene (130 mL) was heated at 105° C. overnight. The reaction mixture was then concentrated, and the resulting solid was washed with diethyl ether and n-pentane to yield the title product as a solid (10.0 g).

Workup

customprepared
concentrationThe reaction mixture was then concentrated
washthe resulting solid was washed with diethyl ether and n-pentane

Sources & evidence

ORD record: ord-638fa86b8c2049dcb3c4ce048d34aad4
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08921360B2

Reaction notes

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