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

HRID 1416011Notes

Reaction equation

HRID 1416011 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.[CH3:21][N:22]=[C:23]=[O:24].CCCC[Sn](O[Sn](CCCC)(CCCC)CCCC)(CCCC)CCCC>O1CCCC1>[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:23](=[O:24])[NH:22][CH3:21])=[N:12][C:11]=2[CH:18]([CH3:20])[CH3:19])[CH:3]=[C:2]([Cl:1])[CH:7]=1

Participants

5

Reactant 3

HCID 12228Methyl IsocyanateHCID 473916(5-(3,5-Dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-yl)methanolHCID 16682746Bis(tributyltin) oxide

Product 1

HCID 4739525-(3,5-Dichlorophenylthio)-4-isopropyl-1-methyl-2-(N-methylcarbamoyl)oxymethyl-1H-imidazoleYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In dry tetrahydrofuran (6 ml)was dissolved 0.300 g (0.91 mmol)of [5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-yl]methanol (Compound I-8)and 0.48 ml (8.15 mmol) of methylisocyanate. To this solution was added 0.04 ml of bis(tributyltin)oxide, and the mixture was stirred at room temperature for 2.5 hours. The reaction mixture was concentrated under reduced pressure. The residue was fractionated by silica gel chromatography (acetone:methylene chloride=1:4), and recrystallized from isopropyl ether to obtain 0.345 g of (Compound I-43)(yield 98%). mp 112-113° C.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customrecrystallized from isopropyl ether
  3. customto obtain 0.345 g of (Compound I-43)(yield 98%)

Sources & evidence

ORD record
ord-ea6b610e47d1439c882578b7ab3904b5
Source dataset
uspto-grants-1999_06
Patent number
US05910506

Reaction notes

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