Ethyl isocyanate → HCID 58909990, compound

HRID 1296026Notes

Reaction equation

HRID 1296026 reaction equation
C(N(CC)CC)C.[CH2:8]([N:10]=[C:11]=[O:12])[CH3:9].[C:13]([C:17]1[CH:18]=[C:19]([C:27](=[O:29])[CH3:28])[CH:20]=[C:21]([O:24][CH2:25][CH3:26])[C:22]=1[OH:23])([CH3:16])([CH3:15])[CH3:14].[Br-:30].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC>C(Cl)Cl.C(Cl)Cl.CO.C(OCC)(=O)C>[CH2:8]([NH:10][C:11](=[O:12])[O:23][C:22]1[C:21]([O:24][CH2:25][CH3:26])=[CH:20][C:19]([C:27](=[O:29])[CH2:28][Br:30])=[CH:18][C:17]=1[C:13]([CH3:14])([CH3:16])[CH3:15])[CH3:9]

Participants

8

Reactant 4

HCID 8022Ethyl isocyanateHCID 8471TriethylamineHCID 23500184Tetra-n-butylammonium tribromideHCID 58910060HCID 58910060, compound

Product 1

HCID 58909990HCID 58909990, compound

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

Triethylamine (0.02 ml, 0.130 mmol) and ethyl isocyanate (0.053 ml, 0.677 ml) were added to a solution of 1-[3-(tert-butyl)-5-ethoxy-4-hydroxyphenyl]-1-ethanone (100 mg, 0.423 mmol) in methylene chloride (4.2 ml) and the mixture was stirred at room temperature for 2 days. Ethyl acetate was added, and then the reaction mixture was washed with water, the organic layer was dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. Tetra-n-butylammonium tribromide (214 mg, 444 mmol) was added to a solution of the residue in methylene chloride-methanol (5 ml:1.2 ml) and the mixture was stirred at room temperature for 8 hours. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield the title compound (142 mg) as colorless crystals.

Workup

  1. washthe reaction mixture was washed with water
  2. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. stirringthe mixture was stirred at room temperature for 8 hours
  5. distillationAfter distilling off the solvent under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-834ac0f9174c4a7b891d6d7f3eb1f446
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

Loading…