Dimethylformamide → N-[2,3,6-Trimethyl-4-[[2-methyl-3-(4-methylphenyl)-2-propenyl]oxy]phenyl]formamide

HRID 29119Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([NH:9][CH:10]=[O:11])=[C:4]([CH3:12])[C:3]=1[CH3:13].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.Cl[CH2:26][C:27]([CH3:36])=[CH:28][C:29]1[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=1>C1(C)C=CC=CC=1.O>[CH3:12][C:4]1[C:3]([CH3:13])=[C:2]([O:1][CH2:26][C:27]([CH3:36])=[CH:28][C:29]2[CH:30]=[CH:31][C:32]([CH3:35])=[CH:33][CH:34]=2)[CH:7]=[C:6]([CH3:8])[C:5]=1[NH:9][CH:10]=[O:11]

Participants

Conditions

Temperature: 50 °C

Procedure

To a mixture of N-(4-hydroxy-2,3,6-trimethylphenyl)formamide (660.4 g), potassium carbonate (1019 g) and dimethylformamide (3302 ml) was added a solution of 1-(3-chloro-2-methyl-1-propenyl)-4-methylbenzene (755 g) in toluene (675 ml), and the mixture was stirred at 50° C. for 14 hr. Water (5944 ml) was then added thereto and the mixture was stirred at 30° C. for 1 hr. The precipitated crystals were collected by filtration and washed with water and isopropylether to give the title compound (940 g, yield 74.5%).

Workup

stirringthe mixture was stirred at 30° C. for 1 hr
filtrationThe precipitated crystals were collected by filtration
washwashed with water and isopropylether

Sources & evidence

ORD record: ord-63c2819b8d404cafaa4e24dfc1980e78
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07420070B2

Reaction notes

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