Reaction #1286788

ord-0000cb7a202e43a59f93335dbb35daa0

Reaction equation

COc1cc(CCl)nc(NC(=O)NS(=O)(=O)c2ccccc2S(=O)(=O)N(C)C)n1
N-(2-dimethylsulfamoylphenylsulfonyl)-N'-(4-chloromethyl-6-methoxy-pyrimidin-2-yl)-urea
CN(C)C(=S)[S-].O.O.[Na+]
dimethyldithiocarbamic acid sodium salt dihydrate
→
COc1cc(CSC(=S)N(C)C)nc(NC(=O)NS(=O)(=O)c2ccccc2S(=O)(=O)N(C)C)n1
N-(2-Dimethylsulfamoylphenyl-sulfonyl)-N'-(4-methoxy-6-dimethylthiocarbamoylthiomethyl-pyrimidin-2-yl)-urea

Reactants

COc1cc(CCl)nc(NC(=O)NS(=O)(=O)c2ccccc2S(=O)(=O)N(C)C)n1
N-(2-dimethylsulfamoylphenylsulfonyl)-N'-(4-chloromethyl-6-methoxy-pyrimidin-2-yl)-urea
CN(C)C(=S)[S-].O.O.[Na+]
dimethyldithiocarbamic acid sodium salt dihydrate

Reagents

None

Solvents

O
water
CC#N
acetonitrile

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Otherthe precipitated product is separated

Procedure

A mixture of 9.3 g of N-(2-dimethylsulfamoylphenylsulfonyl)-N'-(4-chloromethyl-6-methoxy-pyrimidin-2-yl)-urea and 3.7 g of dimethyldithiocarbamic acid sodium salt dihydrate is stirred in 100 ml of acetonitrile at 20°-25° C. for 3 hours. In further processing, the reaction mixture is diluted with 1 litre of water, and the precipitated product is separated. The yield is 10.0 g (91% of theory) of N-(2-dimethylsulfamoylphenyl-sulfonyl)-N'-(4-methoxy-6-dimethylthiocarbamoylthiomethyl-pyrimidin-2-yl)-urea m.p. 181°-183° C. (decomp.).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04902336uspto-grants-1990_02