Triethylamine → 10-([1,1'-Biphenyl]-4-ylcarbonyl)-10,11-dihydrodibenz[b,f][1,4]oxazepine

HRID 1457683Notes

Reaction equation

HRID 1457683 reaction equation
[CH:1]1[C:6]2[CH2:7][NH:8][C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=3[O:11][C:5]=2[CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[C:23]1([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:28]=[CH:27][C:26]([C:29](Cl)=[O:30])=[CH:25][CH:24]=1>C(Cl)Cl.C(Cl)(Cl)Cl>[C:23]1([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:24]=[CH:25][C:26]([C:29]([N:8]2[CH2:7][C:6]3[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=3[O:11][C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]2=3)=[O:30])=[CH:27][CH:28]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 841514-Phenylbenzoyl chlorideHCID 64893310,11-Dihydrodibenzo(b,f)(1,4)oxazepine

Product 1

HCID 2209956210-([1,1'-Biphenyl]-4-ylcarbonyl)-10,11-dihydrodibenz[b,f][1,4]oxazepineYield 83.6%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a cooled (0° C.) solution of 1.0 g of 10,11-dihydrodibenz[b,f][1,4]oxazepine and 7 ml of triethylamine in 30 ml of CH2Cl2 under argon is added dropwise 2.0 g of [1,1'-biphenyl]-4-carbonyl chloride. The mixture is stirred at room temperature for 16 hours and diluted with 50 ml of CHCl3. The mixture is washed with 30 ml each of H2O, 2NHCl, H2O, saturated NaHCO3, H2O, and dried (Na2SO4). Solvent is removed under vacuum to give 1.6 g of a yellow solid, m.p. 93°-95° C; Mass spectrum (CI), 378(MH+).

Workup

  1. washThe mixture is washed with 30 ml each of H2O
  2. dry with material2NHCl, H2O, saturated NaHCO3, H2O, and dried (Na2SO4)
  3. customSolvent is removed under vacuum

Sources & evidence

ORD record
ord-31023d15da084e1383be49dffd1f81a4
Source dataset
uspto-grants-1998_12
Patent number
US05849735

Reaction notes

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