Triethylamine → HCID 67694588, compound

HRID 1457580Notes

Reaction equation

HRID 1457580 reaction equation
[C:1]([Cl:6])(=[O:5])[O:2][CH2:3][CH3:4].[CH:7]1([N:14]([C:31]2[CH:36]=[CH:35][C:34]([N:37]([CH3:39])[CH3:38])=[CH:33][CH:32]=2)[C:15](=[O:30])[NH:16][C:17]2[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[C:19]([C:25]([CH3:28])([CH3:27])[CH3:26])[C:18]=2[OH:29])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.C(N(CC)CC)C>ClCCl>[ClH:6].[CH2:3]([O:2][C:1]([O:29][C:18]1[C:19]([C:25]([CH3:28])([CH3:27])[CH3:26])=[CH:20][C:21]([O:23][CH3:24])=[CH:22][C:17]=1[NH:16][C:15]([N:14]([CH:7]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)[C:31]1[CH:36]=[CH:35][C:34]([N:37]([CH3:39])[CH3:38])=[CH:33][CH:32]=1)=[O:30])=[O:5])[CH3:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 10004070HCID 10004070, compound

Product 1

HCID 67694588HCID 67694588, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under ice-cooling, 1.03 ml of ethyl chlorocarbonate was added dropwise to a mixed solution of 2.45 g of 2-[3-cycloheptyl-3-(4-dimethylaminophenyl)ureido]-4-methoxy-6-tertbutylphenol, 1.51 ml of triethylamine and 50 ml of dichloromethane, and the mixture was stirred at room temperature for 2 hours. After washing and drying, the solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (solvent; chloroform:ethyl acetate=20:1), and precipitated crystals were recrystallized from a mixed solution of isopropyl ether and ethyl acetate. The resulting crystals were dissolved in 50 ml of dichloromethane, and 2 ml of a 4N hydrogen chloride-dioxane solution was added thereto. The mixture was evaporated to dryness under reduced pressure. The residue was crystallized from an isopropyl ether solution to give 1.34 g of O-ethoxycarbonyl-2-[3-cycloheptyl-3-(4-dimethylaminophenyl)ureido]-4-methoxy-6-tert-butylphenol hydrochloride (yield: 44%, melting point: 163°-167° C. (decomposed)).

Workup

  1. temperatureUnder ice-cooling
  2. washAfter washing
  3. customdrying
  4. customthe solvent was removed under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (solvent; chloroform:ethyl acetate=20:1)
  6. customprecipitated crystals
  7. customwere recrystallized from a mixed solution of isopropyl ether and ethyl acetate
  8. dissolutionThe resulting crystals were dissolved in 50 ml of dichloromethane
  9. addition2 ml of a 4N hydrogen chloride-dioxane solution was added
  10. customThe mixture was evaporated to dryness under reduced pressure
  11. customThe residue was crystallized from an isopropyl ether solution

Sources & evidence

ORD record
ord-5fa6848a4d57448fb624bed1d7125e9e
Source dataset
uspto-grants-1998_12
Patent number
US05849732

Reaction notes

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