Phenyl isocyanate → HCID 13423325, compound

HRID 1284468Notes

Reaction equation

HRID 1284468 reaction equation
[C:1]1(/[C:7](/[C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)=[CH:8]\[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][OH:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:21]1([N:27]=[C:28]=[O:29])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(N(CC)CC)C>C(Cl)Cl>[C:21]1([NH:27][C:28]([O:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]/[CH:8]=[C:7](\[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)/[C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)=[O:29])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 13417327HCID 13417327, compound

Product 1

HCID 13423325HCID 13423325, compoundYield 55.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(E)-7-Phenyl-7-(3-pyridyl)-6-hepten-1-ol (4 g, 15 mmoles) and phenyl isocyanate (1.6 ml, 15 mmoles) were dissolved in methylene chloride (20 ml), and triethylamine (0.5 ml) was added to the solution. The mixture was stirred at room temperature for 3 hours and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography using isopropyl ether-ethyl acetate (2:1) as the developing solvent and recrystallization of the product from a mixture of ethyl acetate and isopropyl ether gave 1-phenylaminocarbonyloxy-(E)-7-phenyl-7-(3-pyridyl)-6-heptene (3.2 g, 55%)

Workup

  1. concentrationconcentrated under reduced pressure
  2. customas the developing solvent and recrystallization of the product
  3. additionfrom a mixture of ethyl acetate and isopropyl ether

Sources & evidence

ORD record
ord-ef61ebd3799a456bb4d0795c81dab447
Source dataset
uspto-grants-1986_01
Patent number
US04563446

Reaction notes

Loading…