Sodium Chloride → 5-(5-Pyrimidylmethyloxy)-3-benzylthio-1,2,4-thiadiazole

HRID 917339Notes

Reaction equation

HRID 917339 reaction equation
Cl[C:2]1[S:6][N:5]=[C:4]([S:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:3]=1.[N:15]1[CH:20]=[C:19]([CH2:21][OH:22])[CH:18]=[N:17][CH:16]=1.[H-].[Na+].[Cl-].[Na+]>CN(C)C=O>[N:15]1[CH:20]=[C:19]([CH2:21][O:22][C:2]2[S:6][N:5]=[C:4]([S:7][CH2:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[N:3]=2)[CH:18]=[N:17][CH:16]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 121513833-(Benzylsulfanyl)-5-chloro-1,2,4-thiadiazoleHCID 15466386(Pyrimidin-5-yl)methanol

Product 1

HCID 230324595-(5-Pyrimidylmethyloxy)-3-benzylthio-1,2,4-thiadiazoleYield 45.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Into 2 g of N,N-dimethylformamide were dissolved 219 mg of 5-chloro-3-benzylthio-1,2,4-thiadiazole and 200 mg of 5-pyrimidylmethyl alcohol, 44 mg of sodium hydride (60% in oil) was added thereto under ice-cooling, and the reaction mixture was stirred for 30 minutes. After stirring for 5 hours at room temperature, the reaction mixture was added to saturated sodium chloride aqueous solution, and extracted with t-butyl methyl ether. The organic layer was concentrated, and the residue obtained was subjected to silica gel column chromatography to give 130 mg of 5-(5-pyrimidylmethyloxy)-3-benzylthio-1,2,4-thiadiazole (hereinafter, referred to as the present compound (38)).

Workup

  1. additionwas added
  2. temperatureunder ice-cooling
  3. stirringAfter stirring for 5 hours at room temperature
  4. extractionextracted with t-butyl methyl ether
  5. concentrationThe organic layer was concentrated
  6. customthe residue obtained

Sources & evidence

ORD record
ord-81303ee41a99498abf3ef8ecfe860a9f
Source dataset
uspto-grants-2007_09
Patent number
US07273879B2

Reaction notes

Loading…