Water → HCID 22099835, compound

HRID 1457692Notes

Reaction equation

HRID 1457692 reaction equation
[NH2:1][C:2]1[CH:24]=[CH:23][C:5]([C:6]([N:8]2[CH2:14][C:13]3[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=3[O:11][C:10]3[CH:19]=[CH:20][CH:21]=[CH:22][C:9]2=3)=[O:7])=[C:4]([Cl:25])[CH:3]=1.[C:26]1([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:27]([C:32](Cl)=[O:33])=[CH:28][CH:29]=[CH:30][CH:31]=1.C(N(CC)C(C)C)(C)C.O>ClCCl>[CH:15]1[C:13]2[CH2:14][N:8]([C:6]([C:5]3[CH:23]=[CH:24][C:2]([NH:1][C:32]([C:27]4[C:26]([C:35]5[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=5)=[CH:31][CH:30]=[CH:29][CH:28]=4)=[O:33])=[CH:3][C:4]=3[Cl:25])=[O:7])[C:9]3[CH:22]=[CH:21][CH:20]=[CH:19][C:10]=3[O:11][C:12]=2[CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 12563768[1,1'-Biphenyl]-2-carbonyl chlorideHCID 22100007HCID 22100007, compound

Product 1

HCID 22099835HCID 22099835, compoundYield 30.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 0.263 g of 10,11-dihydro-10(4-amino-2-chlorobenzoyl)dibenz[b,f][1,4]oxazepine, 0.195 g of [1,1'-bipheny]-2-carbonyl chloride and 0.116 g of N,N-diisopropylethylamine in 7 ml of dichloromethane is stirred at room temperature for 3 hours. The mixture is poured into water and extracted with dichloromethane. The extract is washed with 2N Na2CO3, water, brine and dried (Na2SO4). The solution is filtered through a thin pad of hydrous magnesium silicate (pad washed with dichloromethane). The filtrate is concentrated to dryness to give a yellow solid. The solid is purified by chromatography on thick layer silica gel plates with hexane-ethyl acetate (1:1) as solvent to give 0.12 g of a yellow glass, m.p. 145° C.-188° C.: Anal.found: C, 73.6; H, 4.6; N,5.0; Cl, 6.4.

Workup

  1. extractionextracted with dichloromethane
  2. washThe extract is washed with 2N Na2CO3, water, brine
  3. dry with materialdried (Na2SO4)
  4. filtrationThe solution is filtered through a thin pad of hydrous magnesium silicate (pad washed with dichloromethane)
  5. concentrationThe filtrate is concentrated to dryness
  6. customto give a yellow solid
  7. customThe solid is purified by chromatography on thick layer silica gel plates with hexane-ethyl acetate (1:1) as solvent

Sources & evidence

ORD record
ord-564e38eb06aa48af9e71a6d6bc36626b
Source dataset
uspto-grants-1998_12
Patent number
US05849735

Reaction notes

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