Sodium hydride → 1-(2-Chloro-5-pyridylmethyl)-2-methyl-3-nitroisothiourea

HRID 728989Notes

Reaction equation

HRID 728989 reaction equation
[CH3:1][S:2][C:3](=[N:5][N+:6]([O-:8])=[O:7])[NH2:4].[H-].[Na+].[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18]Cl)=[CH:14][N:13]=1>CS(C)=O>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][NH:4][C:3](=[N:5][N+:6]([O-:8])=[O:7])[S:2][CH3:1])=[CH:14][N:13]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 1554792-Chloro-5-(chloromethyl)pyridineHCID 413384(E/Z)-methyl N'-nitrocarbamimidothioate

Product 1

HCID 1361361971-(2-Chloro-5-pyridylmethyl)-2-methyl-3-nitroisothioureaYield 6.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 2-methyl-3-nitroisothiourea (15.0 g) in dimethylsulfoxide (100 ml) was gradually added sodium hydride (oil free 2.9 g) at 5° C., while being stirred for one hour. Thereafter, 2-chloro-5-chloromethyl pyridine (18.0 g) was added to the solution at a temperature in the range of from 5° to 10° C., followed by overnight stirring thereofat room temperature. After the dimethylsulfoxide in the solution was distilled off under reduced pressure, the resulting residue was purified on a chromatographic column (the eluent was a mixture of ethanol and chloroform), so as to obtain the desired 1-(2-chloro-5-pyridylmethyl)-2-methyl-3-nitroisothiourea (2.0 g) having a melting point in the range of from 141° to 143° C.

Workup

  1. customat 5° C.
  2. waitfollowed by overnight
  3. stirringstirring
  4. customroom temperature
  5. distillationAfter the dimethylsulfoxide in the solution was distilled off under reduced pressure
  6. customthe resulting residue was purified on a chromatographic column (the eluent
  7. additiona mixture of ethanol and chloroform), so as

Sources & evidence

ORD record
ord-72cfb95788c54e798df51e60c1695508
Source dataset
uspto-grants-1991_09
Patent number
US05051434

Reaction notes

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