Sodium hydride → 2,6-Dimethyl-4-(3-hydroxypropylthio)pyridine-N-oxide

HRID 1275575Notes

Reaction equation

HRID 1275575 reaction equation
[H-].[Na+].[OH:3][CH2:4][CH2:5][CH2:6][SH:7].Cl[C:9]1[CH:14]=[C:13]([CH3:15])[N+:12]([O-:16])=[C:11]([CH3:17])[CH:10]=1>CN1CCCC1=O>[CH3:17][C:11]1[CH:10]=[C:9]([S:7][CH2:6][CH2:5][CH2:4][OH:3])[CH:14]=[C:13]([CH3:15])[N+:12]=1[O-:16]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 882113-MercaptopropanolHCID 5878434-Chloro-2,6-dimethylpyridine 1-oxide

Product 1

HCID 221173122,6-Dimethyl-4-(3-hydroxypropylthio)pyridine-N-oxide

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent2×

Procedure

12 g of (60% strength) NaH are added in portions to 50 ml of dry N-methylpyrrolidone (NMP). The mixture is stirred for 10 min. 19 g (0.22 mol) of 3-hydroxypropyl mercaptan are metered in the course of 30 min and the mixture is stirred for a further 30 min until evolution of gas has ended. A solution of 28.8 g (0.2 mol) of 4-chloro-2,6-dimethylpyridine-N-oxide in 150 ml of NMP is then added dropwise in the course of 30 min, and the reaction mixture is stirred for 1 h at RT, then for 1 h at 70° C. and after this for a further 1 h at 100° C.

Workup

  1. customare metered in the course of 30 min
  2. stirringthe mixture is stirred for a further 30 min until evolution of gas
  3. stirringthe reaction mixture is stirred for 1 h at RT
  4. waitfor 1 h at 70° C.
  5. customfor a further 1 h
  6. customat 100° C.

Sources & evidence

ORD record
ord-156b777eebab41de93328373404a25d4
Source dataset
uspto-grants-2000_12
Patent number
US06162809

Reaction notes

Loading…