Sodium hydride → HCID 20393023, compound

HRID 1862983Notes

Reaction equation

HRID 1862983 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH3:21])[C:5]2[C:11](=[O:12])[N:10]([CH3:13])[C:9]3[CH:14]=[C:15]([CH3:19])[C:16]([CH3:18])=[CH:17][C:8]=3[NH:7][C:6]=2[N:20]=1.[H-].[Na+].[CH2:24]([N:26]([CH2:31][CH3:32])[CH2:27][CH2:28][CH2:29]Cl)[CH3:25]>CN(C)C=O>[CH2:24]([N:26]([CH2:31][CH3:32])[CH2:27][CH2:28][CH2:29][N:7]1[C:8]2[CH:17]=[C:16]([CH3:18])[C:15]([CH3:19])=[CH:14][C:9]=2[N:10]([CH3:13])[C:11](=[O:12])[C:5]2[C:4]([CH3:21])=[CH:3][C:2]([CH3:1])=[N:20][C:6]1=2)[CH3:25]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 669183-Chloropropyl(diethyl)amineHCID 23372624HCID 23372624, compound

Product 1

HCID 20393023HCID 20393023, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
50 °C

Procedure

A mixture consisting of 1.8 mg of 6,11-dihydro-2,4,6,8,9-pentamethyl-5H-pyrido[2,3-b][1,5]benzodiazepin-5-one, 30 ml of dimethyl formamide and 0.34 gm of 50% sodium hydride in mineral oil was stirred in a nitrogen atmosphere at 50° C. for 30 minutes. Then, a solution of 1.5 gm of 3-diethylaminopropyl chloride in 15 ml of dimethyl formamide was added dropwise at room temperature, and the mixture was heated on an oil bath at 120° C. for 2 hours and then evaporated in vacuo. The residue was admixed with dilute ammonia, and the mixture was repeatedly extracted with ether. The combined ether extracts were dried with sodium sulfate, the ether was distilled off, and the residue was recrystallized from petroleum ether (m.p. 100°-140° C.), yielding 53% of theory of the compound named in the heading, which had a melting point of 104°-106° C.

Workup

  1. temperaturethe mixture was heated on an oil bath at 120° C. for 2 hours
  2. customevaporated in vacuo
  3. extractionthe mixture was repeatedly extracted with ether
  4. dry with materialThe combined ether extracts were dried with sodium sulfate
  5. distillationthe ether was distilled off
  6. customthe residue was recrystallized from petroleum ether (m.p. 100°-140° C.)
  7. customyielding 53% of theory of the compound

Sources & evidence

ORD record
ord-946780e0377a43a4af75cee4ce5ad33b
Source dataset
uspto-grants-1979_09
Patent number
US04167570

Reaction notes

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