N-[2-(N,N-dimethylsulfamoyl)-phenylsulfonyl]-N'-(4-chloromethyl-6-methoxypyrimidin-2-yl)-urea → N-(2-Dimethylsulfamoylphenyl-sulfonyl)-N'-(4-methoxy-6-dimethylthiocarbamoylthiomethyl-pyrimidin-2-yl)-urea

HRID 2232028

Reaction equation

HRID 2232028 reaction equation
[CH3:1][N:2]([CH3:29])[S:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[S:12]([NH:15][C:16]([NH:18][C:19]1[N:24]=[C:23]([CH2:25]Cl)[CH:22]=[C:21]([O:27][CH3:28])[N:20]=1)=[O:17])(=[O:14])=[O:13])(=[O:5])=[O:4].O.O.[Na+].[CH3:33][N:34]([CH3:38])[C:35](=[S:37])[S-:36]>C(#N)C.O>[CH3:1][N:2]([CH3:29])[S:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[S:12]([NH:15][C:16]([NH:18][C:19]1[N:20]=[C:21]([O:27][CH3:28])[CH:22]=[C:23]([CH2:25][S:37][C:35](=[S:36])[N:34]([CH3:38])[CH3:33])[N:24]=1)=[O:17])(=[O:14])=[O:13])(=[O:5])=[O:4]

Participants

5

Reactant 2

HCID 13884816N-[2-(N,N-dimethylsulfamoyl)-phenylsulfonyl]-N'-(4-chloromethyl-6-methoxypyrimidin-2-yl)-ureaHCID 23693613Sodium dimethyldithiocarbamate dihydrate

Product 1

HCID 20070845N-(2-Dimethylsulfamoylphenyl-sulfonyl)-N'-(4-methoxy-6-dimethylthiocarbamoylthiomethyl-pyrimidin-2-yl)-urea

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

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 liter 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.).

Workup

  1. customthe precipitated product is separated

Sources & evidence

ORD record
ord-e4c39a332030435c8f83e9871f62ca4a
Source dataset
uspto-grants-1988_11
Patent number
US04786315

Linked notes

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