Water → 1H-Imidazole-2-propanol, 1-(2-((aminocarbonyl)oxy)ethyl)-5-((3,5-dichlorophenyl)thio)-4-(1-methylethyl)-, carbamate (ester)

HRID 1857782Notes

Reaction equation

HRID 1857782 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[N:14]([CH2:15][CH2:16][OH:17])[C:13]([CH2:18][CH2:19][CH2:20][OH:21])=[N:12][C:11]=2[CH:22]([CH3:24])[CH3:23])[CH:5]=[C:6]([Cl:8])[CH:7]=1.ClC(Cl)(Cl)C([N:29]=[C:30]=[O:31])=O.[OH2:34].C([N:37]([CH2:40]C)CC)C>C(#N)C>[C:40]([O:17][CH2:16][CH2:15][N:14]1[C:10]([S:9][C:4]2[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[CH:3]=2)=[C:11]([CH:22]([CH3:24])[CH3:23])[N:12]=[C:13]1[CH2:18][CH2:19][CH2:20][O:21][C:30](=[O:31])[NH2:29])(=[O:34])[NH2:37]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 76400Trichloroacetyl isocyanateHCID 4741021H-Imidazole-2-propanol, 5-((3,5-dichlorophenyl)thio)-1-(2-hydroxyethyl)-4-(1-methylethyl)-

Product 1

HCID 4741031H-Imidazole-2-propanol, 1-(2-((aminocarbonyl)oxy)ethyl)-5-((3,5-dichlorophenyl)thio)-4-(1-methylethyl)-, carbamate (ester)Yield 43%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
-40 °C

Procedure

In 5 ml of dry acetonitrile was dissolved 240 mg (0.6 mmol) of the diol (137d), and after the solution was cooled to -40° C., 400 mg (2.11 mmol) of trichloroacetyl isocyanate was added dropwise. After 5 minutes, the temperature was elevated gradually to room temperature arid the mixture was stirred for 1 hour. To the mixture was added 3 ml of water and 1.5 ml of triethylamine and the mixture was heated at 50° C. for 3 hours. The reaction mixture was diluted with ice-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 (ethyl acetate) and recrystallized from ethyl acetate-n-hexane to provide 127 mg (yield 43%) of Compound I-151 as crystals. mp 155-163° C. 1H-NMR (CDCl3 -TMS) δ ppm: 1.26(d,J=7.0 Hz,6H),2.16(m,2H),2.86 (m,2H),3.07(sept,1H),4.14(m ,6H),4.88(brs,4H),6.78(m,2H), 7.11 (m,1H); Elementary analysis (C19H24Cl2N4O4S); Calc. (%): C,48.00,H,5.09,Cl,14.92,N,11.79,S,6.74; Found (%): C,47.96,H,5.19,Cl,14.64,N,11.52,S,6.71.

Workup

  1. customwas elevated gradually to room temperature
  2. temperaturethe mixture was heated at 50° C. for 3 hours
  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 (ethyl acetate)
  9. customrecrystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-6e5a50d190354594b56306b8b351783d
Source dataset
uspto-grants-2000_11
Patent number
US06147097

Reaction notes

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