2-Methoxyethanol → HCID 20187142, compound

HRID 1379980Notes

Reaction equation

HRID 1379980 reaction equation
[Na].Cl[C:3]1[C:8]([S:9]([NH2:12])(=[O:11])=[O:10])=[CH:7][CH:6]=[CH:5][N:4]=1.[CH3:13][O:14][CH2:15][CH2:16][OH:17]>>[CH3:13][O:14][CH2:15][CH2:16][O:17][C:3]1[C:8]([S:9]([NH2:12])(=[O:11])=[O:10])=[CH:7][CH:6]=[CH:5][N:4]=1

Participants

4

Reactant 3

HCID 80192-Methoxyethanol2×HCID 5360545SodiumHCID 122344452-chloropyridine-3-sulfonamide

Product 1

HCID 20187142HCID 20187142, compound

Procedure

4.36 g of a 55% dispersion of sodium in oil is added in portions over 15 minutes and under nitrogen to 25 ml of methyl cellosolve. A solution of 9.6 g of 2-chloro-3-pyridylsulfonamide in 25 ml of methyl cellosolve is then added dropwise, with stirring, to the above dispersion over 5 minutes. The reaction mixture is then stirred for 1 hour at reflux temperature and concentrated in vacuo. The residue is acidified to pH 2 with about 25 ml of aqueous HCl at a temperature below 15° C., then stirred and filtered, affording 11.3 g of the desired 2-(2-methoxyethoxy)-3-pyridylsulfonamide, which is recrystallised from acetonitrile and has a melting point of 102°-103° C.

Workup

  1. stirringThe reaction mixture is then stirred for 1 hour
  2. temperatureat reflux temperature
  3. concentrationconcentrated in vacuo
  4. customis acidified to pH 2 with about 25 ml of aqueous HCl at a temperature below 15° C.
  5. stirringstirred
  6. filtrationfiltered

Sources & evidence

ORD record
ord-b125229404f841818e6a45d286f05489
Source dataset
uspto-grants-1986_04
Patent number
US04579583

Reaction notes

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