Iodoethane → HCID 10220644, compound

HRID 1450173Notes

Reaction equation

HRID 1450173 reaction equation
[H-].[Na+].[CH3:3][C:4]1[C:9]2[NH:10][C:11](=[O:19])[C:12]3[CH:18]=[CH:17][CH:16]=[N:15][C:13]=3[NH:14][C:8]=2[CH:7]=[CH:6][CH:5]=1.[CH2:20](I)[CH3:21]>CN(C=O)C>[CH2:20]([O:19][C:11]1[C:12]2[CH:18]=[CH:17][CH:16]=[N:15][C:13]=2[NH:14][C:8]2[CH:7]=[CH:6][CH:5]=[C:4]([CH3:3])[C:9]=2[N:10]=1)[CH3:21]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 4532707-Methyl-6,11-dihydro-5H-pyrido(2,3-b)(1,5)benzodiazepin-5-one

Product 1

HCID 10220644HCID 10220644, compoundYield 18.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Sodium hydride (80% oil dispersion, 0.13 g, 5.5 mmol) was added at room temperature to a suspension of 6,11-dihydro-7-methyl-5H-pyrido[2,3-b][1,5]benzodiazepin-5-one (1.12 g, 5.0 mmol) in DMF (20 mL) under argon. The reaction mixture was heated at 60° C. for 1 h and then was cooled in an ice-bath before the addition of ethyl iodide (0.86 g, 5.5 mmol). Stirring was continued at room temperature overnight, followed by warming to 60° C. for 1 h. The solution was concentrated in vacuo to near dryness, the residue was poured over ice-water, and the resulting solid was collected, washed with water, and dried. Purification by chromatography (elution with 1% MeOH/CH2Cl2) afforded 0.23 g (18%) of the title compound, which crystallized as yellow needles from petroleum ether (30°-60° C.): m.p. 135°-136° C.

Workup

  1. temperatureby warming to 60° C. for 1 h
  2. concentrationThe solution was concentrated in vacuo
  3. additionthe residue was poured over ice-water
  4. customthe resulting solid was collected
  5. washwashed with water
  6. customdried
  7. customPurification
  8. washby chromatography (elution with 1% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-0469e021ca2949c1be708f08ec1a7ca4
Source dataset
uspto-grants-1997_02
Patent number
US05602113

Reaction notes

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