Triethylamine → N-[4-[(6,11-Dihydro-5H-dibenz[b,e]azepin-5-yl)-carbonyl]phenyl]2-(2-methylpropoxy)benzamide

HRID 355939Notes

Reaction equation

HRID 355939 reaction equation
Cl[C:2]1[CH:10]=[CH:9][C:8]([N+]([O-])=O)=[CH:7][C:3]=1[C:4](O)=[O:5].C(N(CC)CC)C.[CH2:21]([O:25]C(Cl)=O)[CH:22]([CH3:24])[CH3:23].[NH2:29][C:30]1[CH:52]=[CH:51][C:33]([C:34]([N:36]2[CH2:42][CH2:41][C:40]3[CH:43]=[CH:44][CH:45]=[CH:46][C:39]=3[C:38]3[CH:47]=[CH:48][CH:49]=[CH:50][C:37]2=3)=[O:35])=[CH:32][CH:31]=1>C(Cl)Cl.C(OCC)(=O)C.C1(C)C=CC=CC=1>[CH:47]1[C:38]2[CH2:39][C:40]3[CH:43]=[CH:44][CH:45]=[CH:46][C:41]=3[CH2:42][N:36]([C:34]([C:33]3[CH:51]=[CH:52][C:30]([NH:29][C:4](=[O:5])[C:3]4[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=4[O:25][CH2:21][CH:22]([CH3:23])[CH3:24])=[CH:31][CH:32]=3)=[O:35])[C:37]=2[CH:50]=[CH:49][CH:48]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 172872-Chloro-5-nitrobenzoic acidHCID 62365Isobutyl chloroformateHCID 538444955-(4-Aminobenzoyl)-6,7-dihydro-5H-dibenz[b,d]azepine

Product 1

HCID 67624252N-[4-[(6,11-Dihydro-5H-dibenz[b,e]azepin-5-yl)-carbonyl]phenyl]2-(2-methylpropoxy)benzamideYield 57.9%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 0.62 g of 2-chloro-5-nitrobenzoic acid and 0.61 g of triethylamine in 5 ml of methylene chloride is added 0.42 g of isobutylchloroformate at 0° C. The mixture is warmed to room temperature for 30 minutes. A solution of 0.31 g of 5-(4-aminobenzoyl)-6,7-dihydro-5H-dibenz[b,d]azepine in 1 ml of methylene chloride is added followed by 10 mg of N,N-dimethylaminopyridine and 1.0 ml of toluene is added. The mixture is heated at 100° C. for 48 hours. The room temperature reaction mixture is diluted with 15 ml of ethyl acetate and washed with 1N HCl, 1N NaOH, brine and dried (Na2 SO4) and evaporated in vacuo to a residue. The residue is purified by column chromatography on silica gel by elution with 1:2 ethyl acetate-hexane to give 0.28 g of the desired product as a yellow solid. MS(CI):536(M+H).

Workup

  1. additionis added
  2. temperatureThe mixture is heated at 100° C. for 48 hours
  3. customThe room temperature reaction mixture
  4. washwashed with 1N HCl, 1N NaOH, brine
  5. customdried (Na2 SO4)
  6. customevaporated in vacuo to a residue
  7. customThe residue is purified by column chromatography on silica gel by elution with 1:2 ethyl acetate-hexane

Sources & evidence

ORD record
ord-ac5758b40b19496db8121ebaff5f46e4
Source dataset
uspto-grants-1998_11
Patent number
US05834461

Reaction notes

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