Water → HCID 18399138, compound

HRID 1019405Notes

Reaction equation

[CH3:1][NH:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[Cl:10].C([Li])(CC)C.[CH3:17][O:18][C:19]1[CH:20]=[C:21]([CH:24]=[C:25]([O:29][CH3:30])[C:26]=1[O:27][CH3:28])[CH:22]=[O:23].O>O1CCCC1.C1CCCCC1.C(OCC)(=O)C>[CH3:1][NH:2][C:3](=[O:11])[C:4]1[C:9]([CH:22]([OH:23])[C:21]2[CH:20]=[C:19]([O:18][CH3:17])[C:26]([O:27][CH3:28])=[C:25]([O:29][CH3:30])[CH:24]=2)=[CH:8][CH:7]=[CH:6][C:5]=1[Cl:10]

Participants

Conditions

Temperature: -60 °C

Procedure

A solution of N-methyl-2-chlorobenzamide (13.0 g) in tetrahydrofuran (300 ml) is cooled to −70° C., and thereto is added dropwise a 1.3M solution of sec-butyl lithium in cyclohexane (130 ral) over a period of 20 minutes. The mixture is stirred at −60° C. for 30 minutes, and thereto is added dropwise a solution of 3,4,5-trimethoxybenzaldehyde (15.0 g) in tetrahydrofuran (100 ml) over a period of 10 minutes. The mixture is stirred at the same temperature for one hour, and thereto are added water and ethyl acetate (300 ml). The ethyl acetate layer is separated, washed, dried, and concentrated under reduced pressure. The residue is crystallized from diethyl ether to give N-methyl-2-chloro-6-[hydroxy-(3,4,5-trimethoxyphenyl)methyl]benzamide (19.2 g) as listed in Table 54.

Workup

stirringThe mixture is stirred at the same temperature for one hour
customThe ethyl acetate layer is separated
washwashed
customdried
concentrationconcentrated under reduced pressure
customThe residue is crystallized from diethyl ether

Sources & evidence

ORD record: ord-c7f63a1c13bc4c138b36c5914ff1aa53
Source dataset: uspto-grants-2002_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06486155B1

Reaction notes

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