Triethylamine → 10,11-dihydro-10-(4-nitro-3-methoxybenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine

HRID 55252Notes

Reaction equation

HRID 55252 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.C(N(CC)CC)C.[CH3:22][O:23][C:24]1[CH:25]=[C:26]([CH:30]=[CH:31][C:32]=1[N+:33]([O-:35])=[O:34])[C:27](Cl)=[O:28]>C(Cl)Cl>[N+:33]([C:32]1[CH:31]=[CH:30][C:26]([C:27]([N:7]2[C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=3[CH2:10][N:4]3[CH:3]=[CH:2][CH:1]=[C:5]3[CH2:6]2)=[O:28])=[CH:25][C:24]=1[O:23][CH3:22])([O-:35])=[O:34]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 111276553-methoxy-4-nitro-benzoyl ChlorideHCID 1554704810,11-Dihydro-5H-benzo[e]pyrrolo[1,2-a][1,4]diazepine

Product 1

HCID 1071374010,11-dihydro-10-(4-nitro-3-methoxybenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepineYield 104.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.55 g of 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine in 8 ml of methylene chloride is added 0.55 g of triethylamine followed by 0.97 g of 3-methoxy-4-nitrobenzoyl chloride. The reaction mixture is stirred at room temperature for 2 hours and then quenched with 10 ml of 1N NaOH. The methylene chloride layer is evaporated and the resulting suspension filtered. The precipitate is washed with 1N NaOH (2×5 ml), water (3×5 ml) and hexane (2×5 ml). The collected solid is dried in vacuo to give 1.13 g of off-white solid. MS (CI): 364(M+H).

Workup

  1. customquenched with 10 ml of 1N NaOH
  2. customThe methylene chloride layer is evaporated
  3. filtrationthe resulting suspension filtered
  4. washThe precipitate is washed with 1N NaOH (2×5 ml), water (3×5 ml) and hexane (2×5 ml)
  5. customThe collected solid is dried in vacuo

Sources & evidence

ORD record
ord-9c6ae98e5dae4e6bb743c1f1090f4112
Source dataset
uspto-grants-1997_04
Patent number
US05624923

Reaction notes

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