4-Bromobenzoyl chloride → HCID 22219706, compound

HRID 1793991Notes

Reaction equation

HRID 1793991 reaction equation
[CH:1]1[CH:2]=[CH:3][N:4]2[CH2:10][C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[NH:7][CH2:6][C:5]=12.[Br:15][C:16]1[CH:24]=[CH:23][C:19]([C:20](Cl)=[O:21])=[CH:18][CH:17]=1.C(N(CC)C(C)C)(C)C>ClCCl>[CH:1]1[CH:2]=[CH:3][N:4]2[CH2:10][C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[N:7]([C:20]([C:19]3[CH:23]=[CH:24][C:16]([Br:15])=[CH:17][CH:18]=3)=[O:21])[CH2:6][C:5]=12

Participants

5

Reactant 3

HCID 685154-Bromobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 1554704810,11-Dihydro-5H-benzo[e]pyrrolo[1,2-a][1,4]diazepine

Product 1

HCID 22219706HCID 22219706, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

10,11-Dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine (8.83 g, 47.9 mmol) and 4-bromobenzoyl chloride (10.0 g, 45.6 mmol) were dissolved in anhydrous dichloromethane (240 mL) followed by addition of N,N-diisopropylethyl amine (8.74 mL, 50.2 mmol) dropwise over the course of 30 minutes. After stirring at room temperature for four hours, the reaction mixture was washed with 1 N hydrochloric acid, 1 N sodium hydroxide and brine, dried over anhydrous magnesium sulfate, filtered and concentrated. Recrystallization of the residue from ethyl acetate afforded the title compound (15.4 g) as white crystals.

Workup

  1. washthe reaction mixture was washed with 1 N hydrochloric acid, 1 N sodium hydroxide and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customRecrystallization of the residue from ethyl acetate

Sources & evidence

ORD record
ord-150857eb1a90415f9722a66c1e63880d
Source dataset
uspto-grants-2006_04
Patent number
US07022699B2

Reaction notes

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