Acetonitrile → 7-(2-Chloroethoxy)-1-ethyl-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

HRID 69052노트

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HRID 69052 반응식
[CH2:1]([N:3]1[C:9](=[O:10])[C:8]([CH3:12])([CH3:11])[C:7](=[O:13])[N:6]([CH3:14])[C:5]2[CH:15]=[C:16]([OH:19])[CH:17]=[CH:18][C:4]1=2)[CH3:2].C(=O)([O-])[O-].[K+].[K+].C(#N)C.Br[CH2:30][CH2:31][Cl:32]>O>[Cl:32][CH2:31][CH2:30][O:19][C:16]1[CH:17]=[CH:18][C:4]2[N:3]([CH2:1][CH3:2])[C:9](=[O:10])[C:8]([CH3:12])([CH3:11])[C:7](=[O:13])[N:6]([CH3:14])[C:5]=2[CH:15]=1

참가 물질

6

반응물 4

HCID 6342AcetonitrileHCID 78491-Bromo-2-ChloroethaneHCID 11430Potassium CarbonateHCID 686733851-Ethyl-7-hydroxy-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

생성물 1

HCID 706567787-(2-Chloroethoxy)-1-ethyl-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
70 °C

실험 절차

1-Ethyl-7-hydroxy-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione (1.2 g) and potassium carbonate (0.95 g) were added to 50% hydrous acetonitrile (24 ml). The mixture was heated to 70° C. to be dissolved. 1-Bromo-2-chloroethane (1.9 ml) was added, and the mixture was heated under reflux for 7 hours. The reaction mixture was cooled to room temperature. Water was added thereto, followed by extraction by ethyl acetate. The organic layer was dried by sodium sulfate, and condensed under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1→1:1). The purified product was condensed to dryness under reduced pressure to give the title compound (1.4 g) as a colorless oily matter.

후처리

  1. dissolutionto be dissolved
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 7 hours
  4. temperatureThe reaction mixture was cooled to room temperature
  5. extractionfollowed by extraction by ethyl acetate
  6. dry with materialThe organic layer was dried by sodium sulfate, and condensed under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1→1:1)
  8. customcondensed to dryness under reduced pressure

출처 및 근거

ORD 기록
ord-dc5f44baa43445b6a7c5c00cf1c78cc6
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822453B2

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