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

HRID 1459484Notes

Reaction equation

HRID 1459484 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.[N+:22]([C:25]1[CH:33]=[CH:32][C:28]([C:29](Cl)=[O:30])=[CH:27][CH:26]=1)([O-:24])=[O:23]>C(Cl)Cl.C(OCC)(=O)C>[N+:22]([C:25]1[CH:26]=[CH:27][C:28]([C:29]([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:30])=[CH:32][CH:33]=1)([O-:24])=[O:23]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 85024-Nitrobenzoyl chlorideHCID 1554704810,11-Dihydro-5H-benzo[e]pyrrolo[1,2-a][1,4]diazepine

Product 1

HCID 1064038210,11-dihydro-10(4-nitrobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepineYield 88.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3.3 g of 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine in 50 ml of methylene chloride under argon is added 5.0 ml of triethylamine followed by ice bath cooling. A solution of 4.0 g of 4-nitrobenzoyl chloride in 20 ml of methylene chloride is added dropwise. Following complete addition, the ice bath is removed and the reaction mixture stirred at room temperature for 2 hours. The volatiles are removed in vacuo to give a residue which is dissolved in ethyl acetate. The solution is washed with water, 1N HCl, NaHCO3, brine, dried with Na2SO4 and filtered. The filtrate is concentrated in vacuo to a solid which is dissolved in methylene chloride, passed through silica gel and the pad washed with ethyl acetate. The combined filtrate is concentrated in vacuo to give 5.3 g of the desired product as a yellow solid, m.p. 188°-190° C.

Workup

  1. customfollowed by ice bath
  2. temperaturecooling
  3. additionaddition
  4. customthe ice bath is removed
  5. customThe volatiles are removed in vacuo
  6. customto give a residue which
  7. washThe solution is washed with water, 1N HCl, NaHCO3, brine
  8. dry with materialdried with Na2SO4
  9. filtrationfiltered
  10. concentrationThe filtrate is concentrated in vacuo to a solid which
  11. dissolutionis dissolved in methylene chloride
  12. washthe pad washed with ethyl acetate
  13. concentrationThe combined filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-7b1fed6e3fa14d0d8ee757e4eb7bcbbb
Source dataset
uspto-grants-1998_12
Patent number
US05854237

Reaction notes

Loading…