Thionyl Chloride → 2-(2-Bromo-4,5-dimethoxyphenyl)-4,4-dimethyl-4,5-dihydro-1,3-oxazole

Reaction equation

[Br:1][C:2]1[CH:15]=[C:14]([O:16][CH3:17])[C:13]([O:18][CH3:19])=[CH:12][C:3]=1[C:4]([NH:6][C:7]([CH3:11])([CH3:10])[CH2:8][OH:9])=O.S(Cl)(Cl)=O>>[Br:1][C:2]1[CH:15]=[C:14]([O:16][CH3:17])[C:13]([O:18][CH3:19])=[CH:12][C:3]=1[C:4]1[O:9][CH2:8][C:7]([CH3:11])([CH3:10])[N:6]=1

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 123193652-Bromo-N-(1-hydroxy-2-methylpropan-2-yl)-4,5-dimethoxybenzamide

Product 1

HCID 123193672-(2-Bromo-4,5-dimethoxyphenyl)-4,4-dimethyl-4,5-dihydro-1,3-oxazole

Procedure

Reaction of 2-bromo-4,5-dimethoxy-N-(1-hydroxy-2-methyl-2-propyl)benzamide and thionyl chloride by the method described in Example 1b provides 2-(2-bromo-4,5-dimethoxyphenyl)-4,4-dimethyl-2-oxazoline as colorless crystals, m.p. 49°-51°.

Sources & evidence

ORD record: ord-b586e154ad8646b290d3b794ad9c1638
Source dataset: uspto-grants-1976_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03985889

Reaction notes

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