Ethyl Thioglycolate → HCID 21241315, compound

HRID 1761428Notes

Reaction equation

HRID 1761428 reaction equation
[CH3:1][CH2:2][O:3][C:4]([CH2:6][SH:7])=[O:5].[H-].[Na+].Cl[C:11]1[N:16]2[N:17]=[CH:18][N:19]=[C:15]2[N:14]=[C:13]([CH3:20])[CH:12]=1>C(O)C.ClCCl.O>[CH2:2]([O:3][C:4]([CH2:6][S:7][C:11]1[N:16]2[N:17]=[CH:18][N:19]=[C:15]2[N:14]=[C:13]([CH3:20])[CH:12]=1)=[O:5])[CH3:1]

Participants

7

Reactant 3

HCID 12185Ethyl ThioglycolateHCID 24758Sodium hydrideHCID 5201277-chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine

Product 1

HCID 21241315HCID 21241315, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

Ethyl thioglycollate, 1.2 g, is dissolved in 30 ml of dry ethanol, to which 400 mg of sodium hydride (60% in an oil) is added under cooling with ice water and stirred for 10 minutes. Then 1.7 g of 7-chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine and 10 ml of dry dichloromethane are added and stirred for 16 hours. To the reaction mixture, water and dichloromethane are added and the organic layer is separated. The separated organic layer is washed with saline and dried over anhydrous potassium carbonate. The solvent is evaporated under reduced pressure and the residue is purified by column chromatography [on 40 g of silica gel, developed and eluted with ethyl acetate] to give 2.2 g of the desired compound as a colorless powder.

Workup

  1. additionis added
  2. stirringstirred for 16 hours
  3. customthe organic layer is separated
  4. washThe separated organic layer is washed with saline
  5. dry with materialdried over anhydrous potassium carbonate
  6. customThe solvent is evaporated under reduced pressure
  7. customthe residue is purified by column chromatography [on 40 g of silica gel, developed and eluted with ethyl acetate]

Sources & evidence

ORD record
ord-3715ae08be1442abba4548a5a4379b28
Source dataset
uspto-grants-1989_05
Patent number
US04826834

Reaction notes

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