Ethanol → Methyl n,n'-diphenylcarbamimidothioate

HRID 2166543Notes

Reaction equation

HRID 2166543 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([NH:7][C:8]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[S:9])=[CH:3][CH:2]=1.CI.[CH2:19](O)C>O>[CH3:19][S:9][C:8](=[N:7][C:4]1[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=1)[NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 6328Methyl iodideHCID 700999Diphenylthiourea

Product 1

HCID 221767Methyl n,n'-diphenylcarbamimidothioate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 2 l flask were added 342 g of thiocarbanilide, 240 g of methyl iodide and 350 cc of ethanol and the mixture was refluxed for 2 hours. After cooling the mixture to a room temperature, a small amount of water was added and the mixture was allowed to stand to precipitate the raw product, which was then filtered off and dissolved in 12 l of hot water. After filtration, the filtrate was converted to an alkaline solution by addition of NaOH to precipitate the product. The product was filtered and washed well until the filtrate became neutral. After drying, the product was recrystalized in 1 l of ethanol to give S-methyl-N,N'-diphenylisothiourea.

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. customto precipitate the raw product, which
  3. filtrationwas then filtered off
  4. dissolutiondissolved in 12 l of hot water
  5. filtrationAfter filtration
  6. additionthe filtrate was converted to an alkaline solution by addition of NaOH
  7. customto precipitate the product
  8. filtrationThe product was filtered
  9. washwashed well until the filtrate
  10. customAfter drying
  11. customthe product was recrystalized in 1 l of ethanol

Sources & evidence

ORD record
ord-1105de70bcdf44d48bde246d90b98bbd
Source dataset
uspto-grants-1983_06
Patent number
US04387150

Reaction notes

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