Dichloromethane → 2-(6,11-Dihydro-11-oxodibenz[b,e]oxepin-2-yl)ethyl carbanilate

HRID 462497Notes

Reaction equation

HRID 462497 reaction equation
[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][O:5][C:4]2[CH:13]=[CH:14][C:15]([CH2:17][CH2:18][OH:19])=[CH:16][C:3]1=2.C(Cl)Cl.[C:23]1([N:29]=[C:30]=[O:31])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1(C)C=CC=CC=1>[C:30](=[O:31])([O:19][CH2:18][CH2:17][C:15]1[CH:14]=[CH:13][C:4]2[O:5][CH2:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[C:2](=[O:1])[C:3]=2[CH:16]=1)[NH:29][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 7672Phenyl isocyanateHCID 134570122-(6,11-Dihydro-11-oxodibenz[b,e]oxepin-2-yl)ethanol

Product 1

HCID 134570112-(6,11-Dihydro-11-oxodibenz[b,e]oxepin-2-yl)ethyl carbanilateYield 67.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A stirred solution of 2.54 g (0.01 mol) of 2-(6,11-dihydro-11-oxodibenz[b,e]oxepin-2-yl)ethanol of Example 1, 20 ml of sieve dried CH2Cl2 and 1.55 g (0.013 mol) of phenylisocyanate was heated 20 hours under reflux with exclusion of moisture. The cooled solution was concentrated on a rotary evaporator to afford an oil which was dissolved in 10 ml of hot toluene. The solution was seeded with product (previously obtained by the method described herein), stirred until a thick suspension formed and allowed to stand overnight (about 16 hours) at ambient temperature. Filtration and drying in vacuo afforded 2.53 g (67.8%) of a colorless solid of 2-(6,11-dihydro-11-oxodibenz[b,e]oxepin-2-yl)ethyl carbanilate m.p. 98°-99° C.

Workup

  1. temperatureunder reflux with exclusion of moisture
  2. concentrationThe cooled solution was concentrated on a rotary evaporator
  3. customto afford an oil which
  4. custompreviously obtained by the method
  5. customformed
  6. custom(about 16 hours)
  7. customat ambient temperature
  8. filtrationFiltration
  9. customdrying in vacuo

Sources & evidence

ORD record
ord-83148920e24144d59aa569667beeed93
Source dataset
uspto-grants-1985_05
Patent number
US04515946

Reaction notes

Loading…