p-Toluenesulfonyl isocyanate → HCID 22058622, compound

HRID 1828827Notes

Reaction equation

HRID 1828827 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([CH3:23])[N:5]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:12][C:11]=2[Cl:22])[C:6]=1[CH2:7][OH:8].[C:24]1([CH3:36])[CH:29]=[CH:28][C:27]([S:30]([N:33]=[C:34]=[O:35])(=[O:32])=[O:31])=[CH:26][CH:25]=1>O1CCOCC1>[CH3:36][C:24]1[CH:29]=[CH:28][C:27]([S:30]([NH:33][C:34](=[O:35])[O:8][CH2:7][C:6]2[N:5]([CH2:9][C:10]3[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:12][C:11]=3[Cl:22])[C:4]([CH3:23])=[N:3][C:2]=2[Cl:1])(=[O:32])=[O:31])=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 77703p-Toluenesulfonyl isocyanateHCID 22058647HCID 22058647, compound

Product 1

HCID 22058622HCID 22058622, compoundYield 75.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4-Chloro-1-(2-chloro-4-(1-pentyloxy)benzyl)-5-hydroxymethyl-2-methyl-1H-imidazole (150 mg) was dissolved in 1,4-dioxane (1.5 ml) and p-toluenesulfonyl isocyanate (99 mg) was added at room temperature. The reaction mixture was stirred at room temperature for 1 hr and concentrated under reduced pressure. To the residue was added ethanol (5 ml) and the precipitated crystals were collected by filtration. The crystals were dissolved in ethyl acetate (2 ml), and hexane (13 ml) was added on an oil bath at 70° C. The mixture was allowed to cool and the precipitated crystals were collected by filtration. The crystals were dried by heating under reduced pressure to give (4-chloro-1-(2-chloro-4-(1-pentyloxy)benzyl)-2-methyl-1H-imidazol-5-yl)methyl N-(4-methylbenzenesulfonyl)carbamate (176 mg) as colorless crystals.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionTo the residue was added ethanol (5 ml)
  3. filtrationthe precipitated crystals were collected by filtration
  4. dissolutionThe crystals were dissolved in ethyl acetate (2 ml)
  5. additionhexane (13 ml) was added on an oil bath at 70° C
  6. temperatureto cool
  7. filtrationthe precipitated crystals were collected by filtration
  8. customThe crystals were dried
  9. temperatureby heating under reduced pressure

Sources & evidence

ORD record
ord-1c0a7e62692e409cb80118b054fb085e
Source dataset
uspto-grants-2006_06
Patent number
US07060721B1

Reaction notes

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