Iodoethane → HCID 67954059, compound

HRID 1430420Notes

Reaction equation

HRID 1430420 reaction equation
[H-].[Na+].CN(C)[C:5](=O)[CH3:6].[CH2:9]([O:16][C:17]1[C:27]2[NH:26][C:25](=[O:28])[C:24]([CH3:30])([CH3:29])[C:23](=[O:31])[N:22]([CH3:32])[C:21]=2[CH:20]=[CH:19][CH:18]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(I)C>C(OCC)(=O)C.O>[CH2:9]([O:16][C:17]1[C:27]2[N:26]([CH2:5][CH3:6])[C:25](=[O:28])[C:24]([CH3:29])([CH3:30])[C:23](=[O:31])[N:22]([CH3:32])[C:21]=2[CH:20]=[CH:19][CH:18]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

7

Reactant 4

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 31374DimethylacetamideHCID 67954075HCID 67954075, compound

Product 1

HCID 67954059HCID 67954059, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

60% sodium hydride (0.37 g, 8.5 mmol) was added to a N,N-dimethylacetamide (12.5 mL) solution of 6-benzyloxy-1,3,3-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione (2.5 g, 7.7 mmol) under ice cooling, and the mixture was stirred for 30 minutes. Ethyl iodide (0.68 mL, 8.5 mmol) was added dropwise thereto, followed by stirring at 10-20° C. for 2 hours. Water (17.5 mL) was added to the reaction solution, and ethyl acetate (20 mL) was added, followed by ethyl acetate extraction. The resulting organic layer was washed with water, and the solvent was distilled off. An aqueous solution of 70% methanol was added to the resulting residue, and the mixture was heated under reflux for 1 hour, followed by stirring for 30 minutes under ice cooling. Crystals were collected by filtration, then washed with an aqueous solution of 70% methanol, and dried at 60° C., thereby obtaining 2.71 g of a white, powdery target compound (yield: 100%).

Workup

  1. stirringby stirring at 10-20° C. for 2 hours
  2. additionwas added
  3. extractionfollowed by ethyl acetate extraction
  4. washThe resulting organic layer was washed with water
  5. distillationthe solvent was distilled off
  6. additionAn aqueous solution of 70% methanol was added to the resulting residue
  7. temperaturethe mixture was heated
  8. temperatureunder reflux for 1 hour
  9. stirringby stirring for 30 minutes under ice cooling
  10. filtrationCrystals were collected by filtration
  11. washwashed with an aqueous solution of 70% methanol
  12. customdried at 60° C.

Sources & evidence

ORD record
ord-380b802dbc1c4d67b2bf1028c5e226cb
Source dataset
uspto-grants-2015_01
Patent number
US08940889B2

Reaction notes

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