Diethyl Sulfate → HCID 67954048, compound

HRID 1430406Notes

Reaction equation

HRID 1430406 reaction equation
[CH3:1][C:2](C)([O-])C.[Na+].CN(C)C=O.[CH2:12]([O:19][C:20]1[CH:21]=[CH:22][C:23]2[NH:29][C:28](=[O:30])[CH2:27][C:26](=[O:31])[N:25]([CH3:32])[C:24]=2[CH:33]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.S(OCC)(OCC)(=O)=O>C(OCC)(=O)C.O>[CH2:12]([O:19][C:20]1[CH:21]=[CH:22][C:23]2[N:29]([CH2:1][CH3:2])[C:28](=[O:30])[CH2:27][C:26](=[O:31])[N:25]([CH3:32])[C:24]=2[CH:33]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 6163Diethyl SulfateHCID 6228DimethylformamideHCID 23676156Sodium t-butoxideHCID 67953980HCID 67953980, compound

Product 1

HCID 67954048HCID 67954048, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium t-butoxide (330 mg, 3.43 mmol) was added to a N,N-dimethylformamide (5 mL) solution of 8-benzyloxy-1-methyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione (1.01 g, 3.4 mmol) under ice cooling, and the mixture was stirred under ice cooling for 30 minutes. Thereafter, diethyl sulfate (0.51 mL, 3.69 mmol) was added, and the mixture was stirred for 6 hours under ice cooling. Water was added to the reaction solution, and ethyl acetate (20 mL) extraction was performed. The resulting organic layer was washed with water, and the solvent was distilled off under reduced pressure. The resulting residue was recrystallized from 50% ethanol (9 mL). Precipitated crystals were collected by filtration, washed with 50% ethanol, and dried at 60° C., thereby obtaining 760 mg of light-yellow, powdery 7-benzyloxy-1-ethyl-5-methyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione (yield: 69%).

Workup

  1. stirringthe mixture was stirred for 6 hours under ice cooling
  2. washThe resulting organic layer was washed with water
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe resulting residue was recrystallized from 50% ethanol (9 mL)
  5. customPrecipitated crystals
  6. filtrationwere collected by filtration
  7. washwashed with 50% ethanol
  8. customdried at 60° C.

Sources & evidence

ORD record
ord-dcb0398fe4bc4eb1a85cd883a8b81b29
Source dataset
uspto-grants-2015_01
Patent number
US08940889B2

Reaction notes

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