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

HRID 1430411Notes

Reaction equation

HRID 1430411 reaction equation
CN(C)C(=O)C.[CH3:7][C:8]([CH3:15])([C:12](Cl)=[O:13])[C:9](Cl)=[O:10].[CH2:16]([O:23][C:24]1[CH:29]=[C:28]([NH:30][CH3:31])[C:27]([NH2:32])=[CH:26][CH:25]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>O>[CH2:16]([O:23][C:24]1[CH:25]=[CH:26][C:27]2[NH:32][C:12](=[O:13])[C:8]([CH3:15])([CH3:7])[C:9](=[O:10])[N:30]([CH3:31])[C:28]=2[CH:29]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 31374Dimethylacetamide2×HCID 4523180Dimethylmalonyl DichlorideHCID 679539775-benzyloxy-N1-methylbenzene-1,2-diamine

Product 1

HCID 679541548-Benzyloxy-1,3,3-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dioneYield 57.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under ice cooling, a N,N-dimethylacetamide (3 mL) solution of dimethylmalonic acid dichloride (0.68 g, 4.0 mmol) was added dropwise to a N,N-dimethyl acetamide (5 mL) suspension of 5-benzyloxy-N1-methylbenzene-1,2-diamine 1/2 sulfate (1.11 g, 4.0 mmol). After the reaction solution was stirred at the same temperature for 4 hours, water (8 mL) was added. The mixture was stirred at 10° C. or less for 30 minutes, and precipitated crystals were collected by filtration. The resulting crystals were washed with water, and dried at 60° C., thereby obtaining 0.75 g of a slightly pink, powdery target compound (yield: 57.8%).

Workup

  1. stirringThe mixture 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. customdried at 60° C.

Sources & evidence

ORD record
ord-46fd459986854fc4b2fd7266bf885bc8
Source dataset
uspto-grants-2015_01
Patent number
US08940889B2

Reaction notes

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