Water → 1H-Imidazole-2-methanol, 5-((3,5-dichlorophenyl)thio)-4-(1-methylethyl)-1-((2-methyl-3-pyridinyl)methyl)-, carbamate (ester)

HRID 1416064Notes

Reaction equation

HRID 1416064 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[N:14]([CH2:15][C:16]3[C:17]([CH3:22])=[N:18][CH:19]=[CH:20][CH:21]=3)[C:13]([CH2:23][OH:24])=[N:12][C:11]=2[CH:25]([CH3:27])[CH3:26])[CH:5]=[C:6]([Cl:8])[CH:7]=1.ClC(Cl)(Cl)[C:30]([N:32]=C=O)=[O:31].C(N(CC)CC)C.O>O1CCCC1.CO>[C:30]([O:24][CH2:23][C:13]1[N:14]([CH2:15][C:16]2[C:17]([CH3:22])=[N:18][CH:19]=[CH:20][CH:21]=2)[C:10]([S:9][C:4]2[CH:3]=[C:2]([Cl:1])[CH:7]=[C:6]([Cl:8])[CH:5]=2)=[C:11]([CH:25]([CH3:27])[CH3:26])[N:12]=1)(=[O:31])[NH2:32]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 76400Trichloroacetyl isocyanateHCID 4740621H-Imidazole-2-methanol, 5-((3,5-dichlorophenyl)thio)-4-(1-methylethyl)-1-((2-methyl-3-pyridinyl)methyl)-

Product 1

HCID 4740631H-Imidazole-2-methanol, 5-((3,5-dichlorophenyl)thio)-4-(1-methylethyl)-1-((2-methyl-3-pyridinyl)methyl)-, carbamate (ester)

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-40 °C

Procedure

In 20 ml of tetrahydrofuran was dissolved 405 mg of 5-(3,5-dichlorophenylthio)-2-hydroxymethyl-4-isopropyl-1-(2-methylpyridin-3-ylmethyl)-1H-imidazole (119a), and the mixture was cooled to -40° C. With stirring, 171 μl of trichloroacetylisocyanate was added, the mixture was allowed to stand to reach room temperature, and stirred for 30 minutes. There were added 200 μl of triethylamine, 5 ml of water and 10 ml of methanol, and the mixture was stirred at 70° C. for 2 hours. After completion of the reaction, the solution was distilled off under reduced pressure, an aqueous sodium hydrogen carbonate solution was added, extracted with ethyl acetate, the extract was dried over sodium sulfate, and the solvent was distilled off under reduced pressure. The crystals were washed with diethyl ether, filtered, and 400 mg of Compound I-133 was obtained (yield 90%). mp 127° C.

Workup

  1. customto reach room temperature
  2. stirringstirred for 30 minutes
  3. stirringthe mixture was stirred at 70° C. for 2 hours
  4. customAfter completion of the reaction
  5. distillationthe solution was distilled off under reduced pressure
  6. additionan aqueous sodium hydrogen carbonate solution was added
  7. extractionextracted with ethyl acetate
  8. dry with materialthe extract was dried over sodium sulfate
  9. distillationthe solvent was distilled off under reduced pressure
  10. washThe crystals were washed with diethyl ether
  11. filtrationfiltered
  12. customwas obtained (yield 90%)

Sources & evidence

ORD record
ord-bed1e1495f6a4325bef3849020dfccb3
Source dataset
uspto-grants-1999_06
Patent number
US05910506

Reaction notes

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