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

HRID 1973248Notes

Reaction equation

HRID 1973248 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 1A 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 was extracted with methylene chloride. The combined extracts were dried and the solvent was evaporated to give a crystalline solid which was triturated with ethyl acetate, then ethanol, to yield 1-methyl-2-(nitro(phenylthio)methylene)imidazolidine (1B) 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 was extracted with methylene chloride
  4. customThe combined extracts were dried
  5. customthe solvent was evaporated
  6. customto give a crystalline solid which
  7. customwas triturated with ethyl acetate

Sources & evidence

ORD record
ord-10851a51b61841f68b7df67583548852
Source dataset
uspto-grants-1976_12
Patent number
US03996372

Reaction notes

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