Sodium hydride → HCID 23434360, compound

HRID 2121838Notes

Reaction equation

HRID 2121838 reaction equation
[NH2:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[C:4]([CH3:10])[CH:3]=1.[H-].[Na+].Br[C:14]1[S:18][N:17]=[C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:15]=1>CN(C)C=O>[CH3:8][C:7]1[CH:6]=[C:5]([O:9][C:14]2[S:18][N:17]=[C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:15]=2)[C:4]([CH3:10])=[CH:3][C:2]=1[NH2:1]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 765444-Amino-2,5-dimethylphenolHCID 22481213101494-82-0

Product 1

HCID 23434360HCID 23434360, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Amino-2,5-dimethylphenol (10.5 g) is added at room temperature to a suspension of sodium hydride (60% dispersion in mineral oil, 3 g) in anhydrous dimethylformamide (300 ml). The reaction mixture is stirred for 30 minutes and 5-bromo-3-phenyl-1,2,4-thiadiazole (18 g) prepared according to Chem. Ber. 1961, 94, 2043 is then added slowly. After stirring for 15 h, the reaction mixture is diluted in ice-water and then extracted with diethyl ether. Drying over magnesium sulphate followed by concentration of the combined organic phases gives the title compound.

Workup

  1. addition1961, 94, 2043 is then added slowly
  2. stirringAfter stirring for 15 h
  3. extractionextracted with diethyl ether
  4. dry with materialDrying over magnesium sulphate

Sources & evidence

ORD record
ord-b4daaf30fdff4bb888311c1fd5417285
Source dataset
uspto-grants-2004_02
Patent number
US06696487B2

Reaction notes

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