Benzenesulfenyl chloride → 1-Methyl-2-[nitro(phenylsulfanyl)methylidene]imidazolidine

HRID 918042Notes

Reaction equation

HRID 918042 reaction equation
[C:1]1([S:7]Cl)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:9][N:10]1[CH2:14][CH2:13][NH:12][C:11]1=[CH:15][N+:16]([O-:18])=[O:17]>N1C=CC=CC=1>[CH3:9][N:10]1[CH2:14][CH2:13][NH:12][C:11]1=[C:15]([N+:16]([O-:18])=[O:17])[S:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 11008040Benzenesulfenyl chlorideHCID 702500461-Methyl-2-(nitromethylidene)imidazolidine

Product 1

HCID 706390091-Methyl-2-[nitro(phenylsulfanyl)methylidene]imidazolidine

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

14.6 g of phenylsulfenyl chloride was added dropwise to a cooled, stirred solution of 14.3 g of Compound 1 in 250 ml of pyridine. The mixture was allowed to stand overnight at room temperature, then excess pyridine was recovered on a rotary evaporator. The residue was treated with 250 ml of water and the mixture extracted with methylene chloride. The combined extracts were dried and the solvent evaporated to give a crystalline solid which was triturated with ethyl acetate, then ethanol, to yield 25, as a yellow solid, melting point: 170° - 173°.

Workup

  1. customexcess pyridine was recovered on a rotary evaporator
  2. additionThe residue was treated with 250 ml of water
  3. extractionthe mixture extracted with methylene chloride
  4. customThe combined extracts were dried
  5. customthe solvent evaporated
  6. customto give a crystalline solid which
  7. customwas triturated with ethyl acetate

Sources & evidence

ORD record
ord-55756baa408e4d72b2cff268dee583fb
Source dataset
uspto-grants-1976_07
Patent number
US03969354

Reaction notes

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