Sodium hydride → HCID 12881670, compound

HRID 1680908Notes

Reaction equation

HRID 1680908 reaction equation
[CH3:1][N:2]1[C:6](=[S:7])[N:5]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)[C:4](=[O:15])[NH:3]1.[H-].[Na+].[CH3:18][O:19][CH2:20]Br>CN(C=O)C.C(Cl)Cl>[CH3:1][N:2]1[C:6](=[S:7])[N:5]([C:8]2[CH:9]=[CH:10][C:11]([Cl:14])=[CH:12][CH:13]=2)[C:4](=[O:15])[N:3]1[CH2:18][O:19][CH3:20]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 83093Bromomethyl methyl etherHCID 12669668HCID 12669668, compound

Product 1

HCID 12881670HCID 12881670, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To 1-methyl-4-(4-chlorophenyl)-1,2,4-triazolidin-3-one-5-thione (5 g) in 200 ml dry DMF was added 0.91 g sodium hydride. After stirring for 30 minutes, bromomethyl methyl ether (2.63 g) was added dropwise, then heated to reflux for 30 minutes, and stirred overnight at room temperature. The solvent was stripped and the residue was dissolved in methylene chloride, washed with water, and chromatographed on a silica gel column (200 g) by elution with methylene chloride, followed by 2.5% methanol in methylene chloride. Yield: 4.8 g.

Workup

  1. temperatureheated
  2. temperatureto reflux for 30 minutes
  3. stirringstirred overnight at room temperature
  4. washwashed with water
  5. customchromatographed on a silica gel column (200 g) by elution with methylene chloride

Sources & evidence

ORD record
ord-9d4736c13ba74d01aa40957d59ae72fb
Source dataset
uspto-grants-1981_06
Patent number
US04276420

Reaction notes

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