Thionyl Chloride → 4,4-Dimethyl-2-(2-methyl-3-nitrophenyl)-4,5-dihydro-1,3-oxazole

HRID 621461Notes

Reaction equation

HRID 621461 reaction equation
S(Cl)(Cl)=O.O[CH2:6][C:7]([NH:10][C:11](=[O:22])[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[C:13]=1[CH3:21])([CH3:9])[CH3:8]>C(OCC)C>[CH3:9][C:7]1([CH3:8])[CH2:6][O:22][C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[C:13]=2[CH3:21])=[N:10]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 800749N-(2-hydroxy-1,1-dimethylethyl)-2-methyl-3-nitrobenzamide

Product 1

HCID 7993934,4-Dimethyl-2-(2-methyl-3-nitrophenyl)-4,5-dihydro-1,3-oxazoleYield 90.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Thionyl chloride, 37 ml, is added dropwise with stirring to 39.7 g (0.1575 mol) of N-(2-hydroxy-1,1-dimethylethyl)-2-methyl-3-nitrobenzamide. The mixture is allowed to stand overnight, poured into diethylether, filtered and the solvent evaporated to give 33.4 g of 4,5-dihydro-4,4-dimethyl-2-(2-methyl-3-nitrophenyl)oxazole as a pale yellow oil which crystallizes on cooling; mp 60°-61° C.

Workup

  1. filtrationfiltered
  2. customthe solvent evaporated

Sources & evidence

ORD record
ord-91108ac5dd81446997b7ed7a0f2a9e32
Source dataset
uspto-grants-1989_04
Patent number
US04824843

Reaction notes

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