Sodium hydride → HCID 59511233, compound

HRID 1157340Notes

Reaction equation

HRID 1157340 reaction equation
[H-].[Na+].[CH3:3][S:4][C:5]1[N:9]=[C:8]([NH2:10])[N:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:6]=1.Cl.Cl[CH2:19][CH2:20][NH:21][CH2:22][CH2:23]Cl>CN(C=O)C>[CH3:3][S:4][C:5]1[N:9]=[C:8]([N:10]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)[N:7]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:6]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 522769Bis(2-chloroethyl)amine hydrochlorideHCID 28185023-(methylthio)-1-phenyl-1H-1,2,4-triazol-5-amine

Product 1

HCID 59511233HCID 59511233, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

Sodium hydride (4.7 g) was taken in dry DMF (100 ml) and a solution of compound 3-(methylthio)-1-phenyl-1H-1,2,4-triazol-5-amine (4 g in 10 ml of DMF) was added slowly at 0° C. The reaction mixture was stirred for 30 min at 0° C. and a solution of bis (2-chloroethyl) amine hydrochloride (4.15 g) in dry DMF (20 ml) was added very slowly. The reaction mixture was allowed to stir over night at room temperature. The reaction mixture was quenched with cold water (5 ml) and extracted with ethyl acetate (3×40 ml). Evaporation of solvent under reduced pressure gave crude product, which, was purified by column chromatography using methanol\dichloromethane (1:9) as eluent to afford 1-(3-(methylthio)-1-phenyl-1H-1,2,4-triazol-5-yl)piperazine, G-26-In, as brown oil.

Workup

  1. stirringto stir over night at room temperature
  2. customThe reaction mixture was quenched with cold water (5 ml)
  3. extractionextracted with ethyl acetate (3×40 ml)
  4. customEvaporation of solvent under reduced pressure
  5. customgave crude product, which
  6. customwas purified by column chromatography

Sources & evidence

ORD record
ord-2e61c83b6f8a4d889e499d2d3c92f7f5
Source dataset
uspto-grants-2010_10
Patent number
US07807671B2

Reaction notes

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