Iodoethane → 1-Ethyl-7-benzyloxy-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

HRID 2402548Notes

Reaction equation

HRID 2402548 reaction equation
[CH3:1][C:2](C)([O-])C.[Na+].CN(C)C(=O)C.[CH2:13]([O:20][C:21]1[CH:22]=[CH:23][C:24]2[NH:30][C:29](=[O:31])[C:28]([CH3:33])([CH3:32])[C:27](=[O:34])[N:26]([CH3:35])[C:25]=2[CH:36]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(I)C>O>[CH2:13]([O:20][C:21]1[CH:22]=[CH:23][C:24]2[N:30]([CH2:1][CH3:2])[C:29](=[O:31])[C:28]([CH3:33])([CH3:32])[C:27](=[O:34])[N:26]([CH3:35])[C:25]=2[CH:36]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 31374DimethylacetamideHCID 23676156Sodium t-butoxideHCID 679541548-Benzyloxy-1,3,3-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

Product 1

HCID 509432951-Ethyl-7-benzyloxy-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dioneYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under ice cooling, sodium t-butoxide (1.96 g, 20.4 mmol) was added to a N,N-dimethylacetamide (30 mL) solution of 8-benzyloxy-1,3,3-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione (6.0 g, 18.5 mmol), and the mixture was stirred for 30 minutes. 1.63 mL (20.4 mmol) of ethyl iodide was added dropwise. The reaction solution was stirred at 10-20° C. for 4 hours. Water (42 mL) was added to the reaction solution, and the mixture was stirred at 10° C. or less for 30 minutes. Thereafter, precipitated crystals were collected by filtration, and the crystals were added to methanol (60 mL). The resultant was heated under reflux, and stirred at 10° C. or less for 30 minutes. Crystals were collected by filtration, then washed with methanol, and dried at 60° C., thereby obtaining 5.90 g of a white, powdery target compound (yield: 91%).

Workup

  1. stirringThe reaction solution was stirred at 10-20° C. for 4 hours
  2. stirringthe mixture was stirred at 10° C. or less for 30 minutes
  3. customThereafter, precipitated crystals
  4. filtrationwere collected by filtration
  5. additionthe crystals were added to methanol (60 mL)
  6. temperatureThe resultant was heated
  7. temperatureunder reflux
  8. stirringstirred at 10° C. or less for 30 minutes
  9. filtrationCrystals were collected by filtration
  10. washwashed with methanol
  11. customdried at 60° C.

Sources & evidence

ORD record
ord-aa76f363387a4cd4a4b3db2fb72a2b57
Source dataset
uspto-grants-2014_08
Patent number
US08796447B2

Reaction notes

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