Water → N-[4-(Dibenz[b,f][1,4]oxazepin-10(11H)-ylcarbonyl)-phenyl][1,1'-biphenyl]-2-carboxamide

HRID 1457691Notes

Reaction equation

HRID 1457691 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:16]1([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:17]([C:22]([NH:24][C:25]2[CH:33]=[CH:32][C:28]([C:29](Cl)=[O:30])=[CH:27][CH:26]=2)=[O:23])=[CH:18][CH:19]=[CH:20][CH:21]=1.C(N(CC)C(C)C)(C)C.O>ClCCl>[CH:1]1[C:6]2[CH2:7][N:8]([C:29]([C:28]3[CH:27]=[CH:26][C:25]([NH:24][C:22]([C:17]4[C:16]([C:34]5[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=5)=[CH:21][CH:20]=[CH:19][CH:18]=4)=[O:23])=[CH:33][CH:32]=3)=[O:30])[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

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 64893310,11-Dihydrodibenzo(b,f)(1,4)oxazepineHCID 114505014-(2-Phenylbenzoylamino)-benzoylchloride

Product 1

HCID 22099982N-[4-(Dibenz[b,f][1,4]oxazepin-10(11H)-ylcarbonyl)-phenyl][1,1'-biphenyl]-2-carboxamideYield 131.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 0.197 g of 10,11-dihydrodibenz[b,f][1,4]oxazepine and 0.402 g of 4-[([1,1'-biphenyl]-2-carbonyl)amino]benzoyl chloride in 5 ml of dichloromethane (cooled in ice bath) is added dropwise 0.154 g of N,N-diisopropylethylamine in 2 ml of dichloromethane. The mixture is stirred at room temperature under argon for 2 hours. The mixture is poured into water and the organic layer separated. The organic extract is washed with 2N Na2CO3, water, brine and dried (Na2SO4). The solution is filtered through a thin pad of hydrous magnesium silicate and the filter cake washed with dichloromethane. The filtrate is concentrated to dryness to give 0.65 g of solid. The solid is purified by thick layer chromatography on silica gel with hexane-ethyl acetate (2:1) as solvent to give 0.110 g of a glass, m.p. 107° C.-122° C. Anal. Found: C, 80.8; H, 4.9; N,6.0.

Workup

  1. customthe organic layer separated
  2. extractionThe organic extract
  3. washis washed with 2N Na2CO3, water, brine
  4. dry with materialdried (Na2SO4)
  5. filtrationThe solution is filtered through a thin pad of hydrous magnesium silicate
  6. washthe filter cake washed with dichloromethane
  7. concentrationThe filtrate is concentrated to dryness

Sources & evidence

ORD record
ord-e375ac38b0774716ba52f5797d944af0
Source dataset
uspto-grants-1998_12
Patent number
US05849735

Reaction notes

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