4-hydroxy-N-(3-hydroxypropyl)benzamide → 4-(5,6-dihydro-4H-1,3-oxazin-2-yl)phenol

HRID 2165421Notes

Reaction equation

HRID 2165421 reaction equation
O[CH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:14])[C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1>S(Cl)(Cl)=O>[O:14]1[CH2:2][CH2:3][CH2:4][N:5]=[C:6]1[C:7]1[CH:8]=[CH:9][C:10]([OH:13])=[CH:11][CH:12]=1

Participants

3

Reactant 1

HCID 133263004-hydroxy-N-(3-hydroxypropyl)benzamide

Product 1

HCID 1356214904-(5,6-dihydro-4H-1,3-oxazin-2-yl)phenolYield 29.7%

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

A mixture of 37.8 g of N-(3-hydroxypropyl)-4-hydroxybenzamide and 100 ml of thionyl chloride was stirred for 1.5 hours. The reaction mixture was concentrated in vacuo, the solid residue triturated with ethyl acetate, and converted to the free base by treatment with ammonium hydroxide. There was obtained 10.2 g of 4-(5,6-dihydro-4H-1,3-oxazin-2-yl)phenol, m.p. 196°-198° C. (from methanol).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe solid residue triturated with ethyl acetate

Sources & evidence

ORD record
ord-eb02f592783b49b4a0c43cf167635cb4
Source dataset
uspto-grants-1990_07
Patent number
US04939267

Reaction notes

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