Dichloromethane → 7-chloro-2,3-dihydro-2-oxo-5-phenyl-1H-1,4-benzodiazepine-3-carboxylic acid isopropyl ester

HRID 1973290Notes

Reaction equation

HRID 1973290 reaction equation
C[O-].[Na+].Cl.[CH:5](OC(C1N(CCN(CC)CC)C(C2C=CC=CC=2)=C2C=1C=CC(Cl)=C2)=O)(C)C.C(Cl)Cl.[CH2:37]([O:39][C:40]([CH:42]1[N:48]=[C:47]([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[C:46]2[CH:55]=[C:56]([Cl:59])[CH:57]=[CH:58][C:45]=2[NH:44][C:43]1=[O:60])=[O:41])[CH3:38]>C(O)(=O)C>[CH:37]([O:39][C:40]([CH:42]1[N:48]=[C:47]([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[C:46]2[CH:55]=[C:56]([Cl:59])[CH:57]=[CH:58][C:45]=2[NH:44][C:43]1=[O:60])=[O:41])([CH3:5])[CH3:38]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 110682Ethyl 7-chloro-2,3-dihydro-2-oxo-5-phenyl-1H-1,4-benzodiazepine-3-carboxylateHCID 10942334Sodium MethoxideHCID 706209895-Chloro-2-[2-(diethylamino)ethyl]-3-phenylisoindole-1-carboxylic acid isopropyl ester hydrochloride

Product 1

HCID 539649407-chloro-2,3-dihydro-2-oxo-5-phenyl-1H-1,4-benzodiazepine-3-carboxylic acid isopropyl ester

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
25 °C

Procedure

500 Ml. of propanol-(2) are treated with 14 g. of sodium methylate; the methanol formed is removed by concentration in vacuo to half the volume and the suspension obtained is diluted with 250 ml. of methylene chloride. Then, 34.2 g. of 7-chloro-2,3-dihydro-2-oxo-5-phenyl-1H-1,4-benzodiazepine-3-carboxylic acid ethyl ester are added and the mixture is subsequently stirred at 25° C. for 40 minutes. The orange solution is made acidic with glacial acetic acid and evaporated to dryness under reduced pressure. The residue is partitioned between water and chloroform; the organic phase is washed with a saturated aqueous solution of sodium chloride, dried over sodium sulfate and concentrated to dryness. The solid crude product is triturated with ether, removed by filtration, washed with ether and recrystallized from methylene chloride/ether, whereby there is obtained 7-chloro-2,3-dihydro-2-oxo-5-phenyl-1H-1,4-benzodiazepine-3-carboxylic acid isopropyl ester having a melting point of 234°-238° C. (decomposition).

Workup

  1. customis removed by concentration in vacuo to half the volume
  2. customthe suspension obtained
  3. additionis diluted with 250 ml
  4. customevaporated to dryness under reduced pressure
  5. customThe residue is partitioned between water and chloroform
  6. washthe organic phase is washed with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated to dryness
  9. customThe solid crude product is triturated with ether
  10. customremoved by filtration
  11. washwashed with ether
  12. customrecrystallized from methylene chloride/ether

Sources & evidence

ORD record
ord-76f51f519d9a4afc8497e8f91f105b63
Source dataset
uspto-grants-1976_12
Patent number
US03996374

Reaction notes

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