Sodium hydride → HCID 12881670, compound

HRID 2286123Notes

Reaction equation

HRID 2286123 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-bd03725d47f640709e63a818f8b3006e
Source dataset
uspto-grants-1982_04
Patent number
US04326878

Reaction notes

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