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Tetrahydrofuran → 1H-Imidazole-1,2-diethanol, 5-((3,5-dichlorophenyl)thio)-4-(1-methylethyl)-, dicarbamate (ester)

HRID 1857769
Notes
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Reaction equation

HRID 1857769 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][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([N:28]=[C:29]=[O:30])=O.C([N:35]([CH2:38]C)CC)C.[O:40]1CCCC1>O>[C:38]([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:21]([CH3:23])[CH3:22])[N:12]=[C:13]1[CH2:18][CH2:19][O:20][C:29](=[O:30])[NH2:28])(=[O:40])[NH2:35]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 76400Trichloroacetyl isocyanateHCID 22130832HCID 22130832, compound

Product 1

HCID 4740821H-Imidazole-1,2-diethanol, 5-((3,5-dichlorophenyl)thio)-4-(1-methylethyl)-, dicarbamate (ester)Yield 81%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent
2×

Conditions

Temperature
-40 °C

Procedure

In 10 ml of dry tetrahydrofuran was dissolved 1.01 g (2.7 mmol) of the diol (131c). The solution was cooled to -40° C. and 1.52 g (8 mmol) of trichloroacetyl isocyanate was added dropwise. After 5 minutes, the temperature was allowed to increase gradually to room temperature and the mixture was stirred for 1 hour. Then, 2 ml of triethylamine and 4 ml of water were added and the mixture was heated at 50° C. for 3 hours. The reaction mixture was diluted with water and extracted with ethyl acetate. The extract was washed with water, dried over anhydrous 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 1.0 g (yield 81%) of Compound I-147 as crystals. mp 152-1530° C.

Workup

  1. temperatureto increase 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 anhydrous 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-29c51dbf78ef4a2f88f60fbbc6588a3e
Source dataset
uspto-grants-2000_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06147097

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes