Dichloromethane → HCID 131721409, compound

HRID 1740053Notes

Reaction equation

HRID 1740053 reaction equation
[NH2:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([N:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[N:12]3[CH:19]=[CH:20][CH:21]=[C:11]3[CH2:10][CH2:9]2)=[O:7])=[C:4]([Cl:24])[CH:3]=1.C(N(CC)CC)C.[Cl:32][C:33]1[CH:41]=[C:40](Cl)[CH:39]=[CH:38][C:34]=1C(Cl)=O.[OH-:43].[Na+].Cl[CH2:46][Cl:47]>>[CH:18]1[C:13]2[N:12]3[CH:19]=[CH:20][CH:21]=[C:11]3[CH2:10][CH2:9][N:8]([C:6]([C:5]3[C:4]([Cl:24])=[C:3]([C:38]4[CH:39]=[CH:40][CH:41]=[C:33]([Cl:32])[CH:34]=4)[C:46]([Cl:47])=[C:23]([CH:22]=3)[C:2]([NH2:1])=[O:43])=[O:7])[C:14]=2[CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 5

HCID 6344Dichloromethane2×HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 666452,4-Dichlorobenzoyl chlorideHCID 218369946,7-Dihydro-5-(4-amino-2-chlorobenzoyl)-5H-pyrrolo[1,2-a][1,5]benzodiazepin

Product 1

HCID 131721409HCID 131721409, compound

Procedure

To a mixture of 0.10 g of 6,7-dihydro-5-(4-amino-2-chlorobenzoyl)-5H-pyrrolo[1,2-a][1,5]benzodiazepine and 0.06 g of triethylamine in 6 ml of dichloromethane is added 0.10 g of 2,4-dichlorobenzoyl chloride in 0.5 ml of dichloromethane. The mixture is stirred at room temperature for 2 hours and 2 ml of 1 N NaOH is added. The volatiles are removed under vacuum and to the residue is added 2 ml of tetrahydrofuran and 1 ml of methanol. The mixture is stirred at room temperature for 2 hours and the volatiles removed. To the residue is added 2 ml of 1 N NaOH and 5 ml of H2O. The mixture is extracted with ethyl acetate and the extract washed with brine and dried (Na2SO4). The solvent is removed and the solid triturated with diethyl ether-hexane to give 0.15 g of white solid, Mass Spectrum (CI): 510(M+H, Cl35).

Workup

  1. customThe volatiles are removed under vacuum and to the residue
  2. additionis added 2 ml of tetrahydrofuran and 1 ml of methanol
  3. stirringThe mixture is stirred at room temperature for 2 hours
  4. customthe volatiles removed
  5. additionTo the residue is added 2 ml of 1 N NaOH and 5 ml of H2O
  6. extractionThe mixture is extracted with ethyl acetate
  7. washthe extract washed with brine
  8. dry with materialdried (Na2SO4)
  9. customThe solvent is removed
  10. customthe solid triturated with diethyl ether-hexane

Sources & evidence

ORD record
ord-6e5e20e885f345f6acebecea96fed291
Source dataset
uspto-grants-1999_10
Patent number
US05968930

Reaction notes

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