Dimethylacetamide → 8-Benzyloxy-1,3,3-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

HRID 2402546Notes

Reaction equation

HRID 2402546 reaction equation
[CH3:1][C:2]([CH3:9])([C:6](Cl)=[O:7])[C:3](Cl)=[O:4].CN(C)C(=O)C.Cl.[CH2:17]([O:24][C:25]1[CH:30]=[C:29]([NH:31][CH3:32])[C:28]([NH2:33])=[CH:27][CH:26]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O>[CH2:17]([O:24][C:25]1[CH:26]=[CH:27][C:28]2[NH:33][C:6](=[O:7])[C:2]([CH3:9])([CH3:1])[C:3](=[O:4])[N:31]([CH3:32])[C:29]=2[CH:30]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 31374DimethylacetamideHCID 4523180Dimethylmalonyl DichlorideHCID 679539765-benzyloxy-N1-methylbenzene-1,2-diamine hydrochloride

Product 1

HCID 679541548-Benzyloxy-1,3,3-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dioneYield 83%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under ice cooling, dimethylmalonic acid dichloride (9.9 mL, 74.9 mmol) was added dropwise to a N,N-dimethyl acetamide (90 mL) solution of 5-benzyloxy-N1-methylbenzene-1,2-diamine hydrochloride (18.0 g, 68.0 mmol). The mixture was stirred at the same temperature for 2.5 hours, and water (90 mL) was added thereto. The reaction solution was stirred at 10° C. or less for 30 minutes, and precipitated crystals were collected by filtration. The resulting crystals were washed with water, then added to methanol (180 mL), and heated under reflux. The mixture was cooled and stirred at 10° C. or less for 30 minutes, and precipitated crystals were collected by filtration. The resulting crystals were washed with methanol (36 mL), and dried at 60° C., thereby obtaining 18.3 g of a white, powdery target compound (yield: 83%).

Workup

  1. stirringThe reaction solution was stirred at 10° C. or less for 30 minutes
  2. customprecipitated crystals
  3. filtrationwere collected by filtration
  4. washThe resulting crystals were washed with water
  5. additionadded to methanol (180 mL)
  6. temperatureheated
  7. temperatureunder reflux
  8. temperatureThe mixture was cooled
  9. stirringstirred at 10° C. or less for 30 minutes
  10. customprecipitated crystals
  11. filtrationwere collected by filtration
  12. washThe resulting crystals were washed with methanol (36 mL)
  13. customdried at 60° C.

Sources & evidence

ORD record
ord-cf589b4382a9435b893435e08ee42529
Source dataset
uspto-grants-2014_08
Patent number
US08796447B2

Reaction notes

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