Water → HCID 178494236, compound

HRID 1589090Notes

Reaction equation

HRID 1589090 reaction equation
[C:1]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[S:7]([NH:10][C:11]([NH:13][C:14]1[N:19]=[C:18]([O:20][CH3:21])[N:17]=[C:16]([O:22][CH3:23])[N:15]=1)=[S:12])(=[O:9])=[O:8].[Na].[CH3:31]I.O>C(#N)C.C(O)C>[C:1]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[S:7]([NH:10][C:11](=[N:13][C:14]1[N:19]=[C:18]([O:20][CH3:21])[N:17]=[C:16]([O:22][CH3:23])[N:15]=1)[S:12][CH3:31])(=[O:8])=[O:9]

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 5360545SodiumHCID 134220281-(2-Biphenylylsulfonyl) 3-(4,6-dimethoxy-1,3,5-triazin-2-yl)thiourea

Product 1

HCID 178494236HCID 178494236, compoundYield 47.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6342AcetonitrileSolvent

Procedure

4.31 g of 1-(2-biphenylylsulfonyl) 3-(4,6-dimethoxy-1,3,5-triazin-2-yl)thiourea were suspended in 50 ml of dry acetonitrile, and a solution of 0.3 g of metallic sodium in 10 ml of ethanol was added to the suspension, and the mixture was heated under reflux for 30 minutes. After cooling, 1.85 g of methyl iodide were added, and the mixture was heated under reflux for 5 hours. After cooling, the reaction mixture was poured into 100 ml of water, and extracted with methylene chloride. Methylene chloride was distilled off under reduced pressure from the extract, and the residue was recrystallized from ethanol to give 2.1 g of 1-(2-biphenylylsulfonyl) 3-(4,6-dimethoxy-1,3,5-triazin-2-yl) 2-methylisothiourea represented by the following formula: ##STR29##

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 30 minutes
  3. temperatureAfter cooling
  4. temperaturethe mixture was heated
  5. temperatureunder reflux for 5 hours
  6. temperatureAfter cooling
  7. extractionextracted with methylene chloride
  8. distillationMethylene chloride was distilled off under reduced pressure from the extract
  9. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-1b3cfcb6a7f24c4e8a39bb83804bd99c
Source dataset
uspto-grants-1986_02
Patent number
US04568381

Reaction notes

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