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Methyl isothiocyanate → 5-(3,5-Dichlorophenylthio)-4-isopropyl-1-methyl-2-(N-methylthiocarbamoyl)oxymethyl-1H-imidazole

HRID 1857718
Notes
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Reaction equation

HRID 1857718 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[N:14]([CH3:15])[C:13]([CH2:16][OH:17])=[N:12][C:11]=2[CH:18]([CH3:20])[CH3:19])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[H-].[Na+].[CH3:23][N:24]=[C:25]=[S:26].[Cl-].[NH4+]>O1CCCC1.CN(C)C=O>[Cl:8][C:6]1[CH:5]=[C:4]([S:9][C:10]2[N:14]([CH3:15])[C:13]([CH2:16][O:17][C:25](=[S:26])[NH:24][CH3:23])=[N:12][C:11]=2[CH:18]([CH3:20])[CH3:19])[CH:3]=[C:2]([Cl:1])[CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 11167Methyl isothiocyanateHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 473916(5-(3,5-Dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-yl)methanol

Product 1

HCID 30020385-(3,5-Dichlorophenylthio)-4-isopropyl-1-methyl-2-(N-methylthiocarbamoyl)oxymethyl-1H-imidazoleYield 61%

Reagents, catalysts & solvents

1
HCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Procedure

To a dry tetrahydrofuran-dimethylformamide (1:1 v/v, 1 ml) solution of 50 mg (0.15 mmol) of [5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-yl]-methanol (Compound I-8) was added 6.6 mg (0.17 mmol) of 60% sodium hydride under nitrogen atomosphere, and the mixture was stirred at room temperature for 30 minutes. Then, 22 mg (0.3 mmol) of methylisothiocyanate was added under ice-cooling. The mixture was stirred at the same temperature for 30 minutes, and at room temperature for 30 minutes. To the reaction mixture, an aqueous ammonium chloride solution was added to terminate the reaction. The mixture was extracted with diethyl ether. The organic layer was washed with saturated brine and dried over magnesium sulfate. The solvent was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (ethyl acetate:n-hexane=1:1) to give 37 mg of 5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-2-(N-methylthiocarbamoyl)oxymethyl-1H-imidazole (Compound I-44) (yield 60%). mp 119-121° C.

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred at the same temperature for 30 minutes
  3. waitat room temperature for 30 minutes
  4. customto terminate
  5. customthe reaction
  6. extractionThe mixture was extracted with diethyl ether
  7. washThe organic layer was washed with saturated brine
  8. dry with materialdried over magnesium sulfate
  9. concentrationThe solvent was concentrated under reduced pressure
  10. customthe residue was purified by silica gel chromatography (ethyl acetate:n-hexane=1:1)

Sources & evidence

ORD record
ord-a16c0a0efd98475db4387b007c720ac3
Source dataset
uspto-grants-2000_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06147097

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes