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

HRID 637869
Notes
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Reaction equation

HRID 637869 reaction equation
[C:1]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=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]([CH3:20])[CH:17]=[C:16]([CH3:21])[N:15]=1)=[S:12])(=[O:9])=[O:8].[Na].[CH3:29]I.O>C(#N)C.C(O)C>[C:1]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[S:7]([NH:10][C:11](=[N:13][C:14]1[N:15]=[C:16]([CH3:21])[CH:17]=[C:18]([CH3:20])[N:19]=1)[S:12][CH3:29])(=[O:9])=[O:8]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 5360545SodiumHCID 134885341-(2-Biphenylsulfonyl)3-(4,6-dimethylpyrimidin-2-yl)thiourea

Product 1

HCID 178503865methyl N-(4,6-dimethylpyrimidin-2-yl)-N'-(2-phenylphenyl)sulfonylcarbamimidothioateYield 38.8%

Reagents, catalysts & solvents 2

HCID 702
Ethanol
Solvent
HCID 6342AcetonitrileSolvent

Procedure

3.98 g of 1-(2-biphenylylsulfonyl)3-(4,6-dimethylpyrimidin-2-yl)thiourea was suspended in 50 ml of dry acetonitrile, and a solution of 0.3 g of metallic sodium in 10 ml of ethanol was added, and the mixture was heated under reflux for 30 minutes. After cooling, 1.85 g of methyl iodide was added, and the mixture was heated under reflux for 5 hours. The reaction mixture was cooled, and then poured into 100 ml of water. The product was extracted with methylene chloride. Methylene chloride was evaporated under reduced pressure, and the residue was recrystallized from ethanol to give 1.6 g of the desired 1-(2-biphenylylsulfonyl)3-(4,6-dimethylpyrimidin-2-yl)2-methylisothiourea (compound No. II-1) which was the same as obtained in Example 1. mp. 154°-157° C.

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. temperatureThe reaction mixture was cooled
  7. extractionThe product was extracted with methylene chloride
  8. customMethylene chloride was evaporated under reduced pressure
  9. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-89bf74d21d564b4b9206beac4d6bd9e5
Source dataset
uspto-grants-1985_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04559079

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes