4-Nitrobenzoyl chloride → HCID 10343971, compound

HRID 1611900Notes

Reaction equation

HRID 1611900 reaction equation
[N+:1]([C:4]1[CH:33]=[CH:32][C:7]([C:8]([N:10]2[CH2:16][C:15]3[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=3[C:13]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[Cl:27])=[C:12]3[CH2:28][CH:29]=[CH:30][CH:31]=[C:11]23)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].ClC1C=CC=CC=1C1C2C=CC=CC=2CNC2C=CC=CC1=2.C(=O)([O-])[O-].[K+].[K+].[N+](C1C=CC(C(Cl)=O)=CC=1)([O-])=O>C(#N)C.O>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:8]([N:10]2[CH2:16][C:15]3[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=3[CH:13]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[Cl:27])[C:12]3[CH:28]=[CH:29][CH:30]=[CH:31][C:11]2=3)=[O:9])=[CH:32][CH:33]=1)([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 85024-Nitrobenzoyl chlorideHCID 11430Potassium CarbonateHCID 9882976HCID 9882976, compoundHCID 22252225HCID 22252225, compound2×

Product 1

HCID 10343971HCID 10343971, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

preferred method of synthesis of N-(4′-nitrobenzoyl)-11-(2′-chlorophenyl)-5,6-dihydro-1H-dibenz[b,e]azepine (Compound 28) is as follows: A mixture of 0.2 g (0.00065 mole) of 11-(2′-chlorophenyl)-5,6-dihydro-11H-dibenz[b,e]azepine, 0.179 g (0.0013 mole) of potassium carbonate and 0.133 g (0.00072 mole) of 4-nitrobenzoyl chloride in 10 mL of acetonitrile, was stirred at room temperature for 12 hours. The mixture was stirred with 15 mL of water for 10 minutes. The reaction mixture was extracted with ethyl acetate (2×15 mL). The organic layer was dried over magnesium sulfate. Evaporation gave the crude product as a sticky solid. Trituration of the crude product with ethanol and washing the obtained solid with hexane gave 0.148 g (50% yield) of a white solid having a melting point of 178-181° C.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate (2×15 mL)
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. customEvaporation
  4. customgave the crude product as a sticky solid
  5. washTrituration of the crude product with ethanol and washing the obtained solid with hexane

Sources & evidence

ORD record
ord-707dc2f8fdfe4efa9b86d5e70a0619d0
Source dataset
uspto-grants-2006_01
Patent number
US06992079B2

Reaction notes

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