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

HRID 359838Notes

Reaction equation

HRID 359838 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-9c6fc7c29154490b844d19cd9d582ba8
Source dataset
uspto-grants-1991_03
Patent number
US05002960

Reaction notes

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