Triethylamine → HCID 474086, compound

HRID 1857775Notes

Reaction equation

HRID 1857775 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[N:14]([CH2:15][CH3:16])[C:13]([CH2:17][CH2:18][CH2:19][OH:20])=[N:12][C:11]=2[CH:21]([CH3:23])[CH3:22])[CH:5]=[C:6]([Cl:8])[CH:7]=1.ClC(Cl)(Cl)[C:26]([N:28]=C=O)=[O:27].C(N(CC)CC)C>O1CCCC1.O>[C:26]([O:20][CH2:19][CH2:18][CH2:17][C:13]1[N:14]([CH2:15][CH3:16])[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:21]([CH3:22])[CH3:23])[N:12]=1)(=[O:27])[NH2:28]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 76400Trichloroacetyl isocyanateHCID 4740851H-Imidazole-2-propanol, 5-((3,5-dichlorophenyl)thio)-1-ethyl-4-(1-methylethyl)-

Product 1

HCID 474086HCID 474086, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-40 °C

Procedure

In 7 ml of dry tetrahydrofuran was dissolved 700 mg (1.9 mmol) of the alcohol (137b), and after the solution was cooled to -40° C., 530 mg (2.8 mmol) of trichloroacetyl isocyanate was added, the temperature was elevated to room temperature. After 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 and 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 (3% methanol-ethyl acetate) and recrystallized from ethyl acetate-n-hexane to provide 705 mg (yield 90%) of Compound I-149 as crystals. mp 128-129° C.

Workup

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

Sources & evidence

ORD record
ord-303df69df31c4603b0580a23f27c8fb2
Source dataset
uspto-grants-2000_11
Patent number
US06147097

Reaction notes

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