Water → methyl N-(4,6-dimethylpyrimidin-2-yl)-N'-(2-phenylphenyl)sulfonylcarbamimidothioate

HRID 637868Notes

Reaction equation

HRID 637868 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[N:3]=1.[OH-].[Na+].[C:12]1([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[S:18]([N:21]=[C:22](SC)[S:23][CH3:24])(=[O:20])=[O:19].O>CN(C)C=O>[C:12]1([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[S:18]([NH:21][C:22](=[N:1][C:2]1[N:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[N:3]=1)[S:23][CH3:24])(=[O:19])=[O:20]

Participants

6

Reactant 4

HCID 962WaterHCID 130212-Amino-4,6-dimethyl pyrimidineHCID 14798Sodium HydroxideHCID 13422024dimethyl N-(2-biphenylylsulfonyl)carbonimidodithioate

Product 1

HCID 178503865methyl N-(4,6-dimethylpyrimidin-2-yl)-N'-(2-phenylphenyl)sulfonylcarbamimidothioateYield 70.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

12.3 g of 2-amino-4,6-dimethylpyrimidine was suspended in 300 ml of dimethylformamide, and 4 g of sodium hydroxide (oily 60%) was added. The mixture was stirred at room temperature for 1 hour. Furthermore, 33.7 g of dimethyl N-(2-biphenylylsulfonyl)carbonimidodithioate was added, and the mixture was stirred at room temperature for a day and night. The reaction mixture was poured into 2 liters of water, and filtered. When the filtrate was made weakly acidic, white crystals precipitated. The crystals were collected by filtration, and recrystallized from ethanol to give 29.2 g of the desired 1-(2-biphenylylsulfonyl)3-(4,6-dimethylpyrimidin-2-yl)2-methylisothiourea of the following formula, mp. 154°-157° C.: ##STR18##

Workup

  1. stirringthe mixture was stirred at room temperature for a day and night
  2. filtrationfiltered
  3. customwhite crystals precipitated
  4. filtrationThe crystals were collected by filtration
  5. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-67a028b9013c4937aae94ff670b902ae
Source dataset
uspto-grants-1985_12
Patent number
US04559079

Reaction notes

Loading…