Triethylamine → 1H-Imidazole-2-propanol, 5-((3,5-dichlorophenyl)thio)-4-(1-methylethyl)-1-(4-pyridinylmethyl)-, carbamate (ester)

HRID 1857778Notes

Reaction equation

HRID 1857778 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[N:14]([CH2:15][C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)[C:13]([CH2:22][CH2:23][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>O1CCCC1.O>[C:31]([O:25][CH2:24][CH2:23][CH2:22][C:13]1[N:14]([CH2:15][C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=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

6

Reactant 3

HCID 8471TriethylamineHCID 76400Trichloroacetyl isocyanateHCID 4740981H-Imidazole-2-propanol, 5-((3,5-dichlorophenyl)thio)-4-(1-methylethyl)-1-(4-pyridinylmethyl)-

Product 1

HCID 4740991H-Imidazole-2-propanol, 5-((3,5-dichlorophenyl)thio)-4-(1-methylethyl)-1-(4-pyridinylmethyl)-, carbamate (ester)Yield 79.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-40 °C

Procedure

In 7 ml of dry tetrahydrofuran was dissolved 700 mg (1.6 mmol) of the alcohol (137c), and after the solution was cooled to -40° C., 450 mg (2.4 mmol) of trichloroacetyl isocyanate was added and the temperature was elevated gradually to room temperature. After stirring for 30 minutes, 2 ml of water and 1 ml of triethylamine were added and the mixture was stirred at room temperature for 3 days. The reaction mixture was diluted with water and extracted with ethyl acetate. The extract was washed with water, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (5% methanol-ethyl acetate) and recrystallized from ethyl acetate-n-hexane to provide 610 mg (yield 79%) of Compound I-150 as crystals. mp 114-115° C.

Workup

  1. customwas elevated gradually to room temperature
  2. stirringthe mixture was stirred at room temperature for 3 days
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (5% methanol-ethyl acetate)
  9. customrecrystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-b44860d8257f4f6693dce5d09c7bb0c7
Source dataset
uspto-grants-2000_11
Patent number
US06147097

Reaction notes

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