Triethylamine → 6,7-dihydro-5-(2-chloro-4-nitrobenzoyl)-5H-pyrrolo[1,2-a][1,5]benzodiazepine

HRID 1459576Notes

Reaction equation

HRID 1459576 reaction equation
[CH:1]1[C:11]2[N:10]3[CH:12]=[CH:13][CH:14]=[C:9]3[CH2:8][CH2:7][NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[Cl:22][C:23]1[CH:31]=[C:30]([N+:32]([O-:34])=[O:33])[CH:29]=[CH:28][C:24]=1[C:25](Cl)=[O:26]>C(Cl)Cl>[Cl:22][C:23]1[CH:31]=[C:30]([N+:32]([O-:34])=[O:33])[CH:29]=[CH:28][C:24]=1[C:25]([N:6]1[C:5]2[CH:4]=[CH:3][CH:2]=[CH:1][C:11]=2[N:10]2[CH:12]=[CH:13][CH:14]=[C:9]2[CH2:8][CH2:7]1)=[O:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 81522Benzoyl chloride, 2-chloro-4-nitro-HCID 123593416,7-dihydro-5H-pyrrolo[1,2-a][1,5]benzodiazepine

Product 1

HCID 218370306,7-dihydro-5-(2-chloro-4-nitrobenzoyl)-5H-pyrrolo[1,2-a][1,5]benzodiazepineYield 105.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 0.28 g of 6,7-dihydro-5H-pyrrolo[1,2-a][1,5]benzodiazepine in 6 ml of methylene chloride is added 0.30 g of triethylamine followed by 0.50 g of 2-chloro-4-nitrobenzoyl chloride in 0.5 ml of methylene chloride. The reaction mixture is stirred at room temperature for 1 hour then quenched with 5 ml of saturated NaHCO3. The methylene chloride is evaporated in vacuo and the residue is diluted with 5 ml of water and extracted with 20 ml of ethyl acetate. The organic layer is separated, washed with saturated NaHCO3 and brine, dried with Na2SO4 and evaporated in vacuo to give 0.59 g of a yellow foam which is triturated with ether-hexanes to give 0.56 g of the desired product as off-white solid. MS(CI):368(M+H)(Cl35) 370(M+H)(Cl37)

Workup

  1. customthen quenched with 5 ml of saturated NaHCO3
  2. customThe methylene chloride is evaporated in vacuo
  3. additionthe residue is diluted with 5 ml of water
  4. extractionextracted with 20 ml of ethyl acetate
  5. customThe organic layer is separated
  6. washwashed with saturated NaHCO3 and brine
  7. dry with materialdried with Na2SO4
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-1ad63528c9ae4fb0b5072bb1d810084d
Source dataset
uspto-grants-1998_12
Patent number
US05854237

Reaction notes

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