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

HRID 1416058Notes

Reaction equation

HRID 1416058 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[N:14]([CH2:15][CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)[C:13]([CH2:24][OH:25])=[N:12][C:11]=2[CH:26]([CH3:28])[CH3:27])[CH:5]=[C:6]([Cl:8])[CH:7]=1.ClC(Cl)(Cl)[C:31]([N:33]=C=O)=[O:32].C(N(CC)CC)C.O>O1CCCC1.CO>[C:31]([O:25][CH2:24][C:13]1[N:14]([CH2:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=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:26]([CH3:28])[CH3:27])[N:12]=1)(=[O:32])[NH2:33]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 76400Trichloroacetyl isocyanateHCID 474135HCID 474135, compound

Product 1

HCID 4740481H-Imidazole-2-methanol, 5-((3,5-dichlorophenyl)thio)-4-(1-methylethyl)-1-(3-(2-pyridinyl)propyl)-, carbamateYield 83%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-40 °C

Procedure

In 10 ml of tetrahydrofuran was dissolved 110 mg of 5-(3,5-dichlorophenylthio)-4-isopropyl-2-hydroxymethyl-1-(3-(2-pyridyl)propyl)-1H-imidazole, and the mixture was cooled to -40° C. Under stirring, 45.1 μl of trichloroacetylisocyanate was added, the mixture was allowed to warm up to room temperature, and stirred for 30 minutes. Added were 100 μl of triethylamine, 600 μl of water and 600 μl of methanol, and the mixture was stirred at 70° C. for 1 hour. 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 residue was purified by silica gel chromatography (ethyl acetate:methanol=10:1)to give 80 mg of Compound I-130 (yield 83%).

Workup

  1. temperatureto warm up to room temperature
  2. stirringstirred for 30 minutes
  3. additionAdded
  4. stirringthe mixture was stirred at 70° C. for 1 hour
  5. customAfter completion of the reaction
  6. distillationthe solution was distilled off under reduced pressure
  7. additionan aqueous sodium hydrogen carbonate solution was added
  8. extractionextracted with ethyl acetate
  9. dry with materialthe extract was dried over sodium sulfate
  10. distillationthe solvent was distilled off under reduced pressure
  11. customThe residue was purified by silica gel chromatography (ethyl acetate

Sources & evidence

ORD record
ord-90277743fa9642ed9d6b1c444cf9ad8f
Source dataset
uspto-grants-1999_06
Patent number
US05910506

Reaction notes

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