Dichloromethane → HCID 20393031, compound

HRID 1862971Notes

Reaction equation

HRID 1862971 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH3:19])[C:5]2[C:11](=[O:12])[N:10]([CH3:13])[C:9]3[CH:14]=[CH:15][CH:16]=[CH:17][C:8]=3[NH:7][C:6]=2[N:18]=1.[H-].[Na+].Br[CH2:23][CH2:24][CH2:25][Cl:26].C(Cl)Cl>CN(C)C=O>[Cl:26][CH2:25][CH2:24][CH2:23][N:7]1[C:8]2[CH:17]=[CH:16][CH:15]=[CH:14][C:9]=2[N:10]([CH3:13])[C:11](=[O:12])[C:5]2[C:4]([CH3:19])=[CH:3][C:2]([CH3:1])=[N:18][C:6]1=2

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 80061-Bromo-3-chloropropaneHCID 24758Sodium hydrideHCID 20393030HCID 20393030, compound

Product 1

HCID 20393031HCID 20393031, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.47 gm of 6,11-dihydro-2,4,6-trimethyl-5H-pyrido-[2,3-b][1,5]benzodiazepin-5-one were dissolved in 15 ml of dimethyl formamide, 0.76 gm of 50% sodium hydride in mineral oil was added, and the mixture was stirred at room temperature for one hour. Then, 1.7 ml of 1-bromo-3-chloro-propane were added, and the mixture was stirred at room temperature for 5 hours. After standing overnight, 100 ml of methylene chloride were added and the reaction mixture was washed three times with water. The organic phase was dried over sodium sulfate and evaporated in vacuo at room temperature. The crystalline residue was digested with a mixture of 7 ml of chloroform and 7 ml of ethyl acetate, and the mixture was suction-filtered. The filter cake was recrystallized from absolute ethanol, yielding 52% of theory of 11-(3-chloro-propyl)-6,11-dihydro-2,4,6-trimethyl-5H-pyrido[2,3-b][1,5]benzodiazepin-5-one having a melting point of 161°-163° C.

Workup

  1. stirringthe mixture was stirred at room temperature for 5 hours
  2. waitAfter standing overnight
  3. washthe reaction mixture was washed three times with water
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. customevaporated in vacuo at room temperature
  6. additionThe crystalline residue was digested with a mixture of 7 ml of chloroform and 7 ml of ethyl acetate
  7. filtrationthe mixture was suction-filtered
  8. customThe filter cake was recrystallized from absolute ethanol

Sources & evidence

ORD record
ord-8324c6f8015f4fa3952eafc3f5885760
Source dataset
uspto-grants-1979_09
Patent number
US04167570

Reaction notes

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