Thionyl Chloride → HCID 19602325, compound

HRID 1604224Notes

Reaction equation

HRID 1604224 reaction equation
O[CH:2]([CH3:19])[CH2:3][NH:4][C:5]([C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][C:8]=1[O:17][CH3:18])=[O:6].S(Cl)(Cl)=O>CCOCC>[CH3:18][O:17][C:8]1[CH:9]=[CH:10][C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:7]=1[C:5]1[O:6][CH:2]([CH3:19])[CH2:3][N:4]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 53770374HCID 53770374, compound

Product 1

HCID 19602325HCID 19602325, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

This N-(2-hydroxy-1-propyl) 2-methoxy-1-naphthamide (4.00 g, 15.4 mmol) was added in portions to ice-water cooled thionyl chloride (7.4 g, 62 mmol). This was then stirred at room temperature and after 1 hour the slurry which had formed was diluted with ether and collected by filtration, then was partitioned between ether and aqueous sodium hydroxide. This ether solution was dried (MgSO4) and concentrated to afford 2-(2-methoxy-1-naphthyl)-5-methyloxazoline as an oil.

Workup

  1. customhad formed
  2. filtrationcollected by filtration
  3. customwas partitioned between ether and aqueous sodium hydroxide
  4. dry with materialThis ether solution was dried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-316c36ab656446a691ef10d30e44450c
Source dataset
uspto-grants-1999_11
Patent number
US05994270

Reaction notes

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