Triethylamine → 4,10-Dihydro-4-(4-nitrobenzoyl)-5H-pyrrolo[1,2-a]thieno[3,2-e][1,4]diazepin

HRID 1459526Notes

Reaction equation

HRID 1459526 reaction equation
[S:1]1[C:10]2[CH2:9][N:8]3[CH:11]=[CH:12][CH:13]=[C:7]3[CH2:6][NH:5][C:4]=2[CH:3]=[CH:2]1.C(N(CC)CC)C.[N+:21]([C:24]1[CH:32]=[CH:31][C:27]([C:28](Cl)=[O:29])=[CH:26][CH:25]=1)([O-:23])=[O:22]>C(Cl)Cl.C(OCC)(=O)C>[N+:21]([C:24]1[CH:25]=[CH:26][C:27]([C:28]([N:5]2[C:4]3[CH:3]=[CH:2][S:1][C:10]=3[CH2:9][N:8]3[CH:11]=[CH:12][CH:13]=[C:7]3[CH2:6]2)=[O:29])=[CH:31][CH:32]=1)([O-:23])=[O:22]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 85024-Nitrobenzoyl chlorideHCID 218369694,10-Dihydro-5H-pyrrolo[1,2-a]thieno[3,2-e][1,4]diazepine

Product 1

HCID 218370274,10-Dihydro-4-(4-nitrobenzoyl)-5H-pyrrolo[1,2-a]thieno[3,2-e][1,4]diazepin

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3 mmol of 4,10-dihydro-5H-pyrrolo[1,2-a]thieno[3,2-e][1,4]diazepine in 10 ml of methylene chloride under argon is added 5 mmol of triethylamine followed by ice bath cooling. A solution of 3.3 mmol of 4-nitrobenzoyl chloride in 3 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, 2N citric acid, NaHCO3, and brine. The reaction mixture is dried with Na2SO4, filtered and evaporated in vacuo to give a solid which is purified by flash chromatography on silica gel to give desired product as a solid.

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, 2N citric acid, NaHCO3, and brine
  8. dry with materialThe reaction mixture is dried with Na2SO4
  9. filtrationfiltered
  10. customevaporated in vacuo
  11. customto give a solid which
  12. customis purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-ec751a93734e4b3e8211b5220cdb5a4e
Source dataset
uspto-grants-1998_12
Patent number
US05854237

Reaction notes

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