Potassium Carbonate → (E)-but-2-enedioic acid;4-methyl-2-[2-(2-methylpyrrolidin-1-yl)ethyl]-2,3-dihydropyrido[3,2-f][1,4]oxazepine-5-thione;propan-2-ol

HRID 4851

반응식

HRID 4851 반응식
Cl[CH2:2][CH2:3][CH:4]1[CH2:10][N:9]([CH3:11])[C:8](=[S:12])[C:7]2[CH:13]=[CH:14][CH:15]=[N:16][C:6]=2[O:5]1.[CH3:17][CH:18]1[CH2:22][CH2:21][CH2:20][NH:19]1.C(=O)([O-])[O-].[K+].[K+].[C:29]([OH:36])(=[O:35])/[CH:30]=[CH:31]/[C:32]([OH:34])=[O:33]>C(O)C>[CH3:3][CH:4]([OH:5])[CH3:10].[C:29]([OH:36])(=[O:35])/[CH:30]=[CH:31]/[C:32]([OH:34])=[O:33].[CH3:11][N:9]1[C:8](=[S:12])[C:7]2[CH:13]=[CH:14][CH:15]=[N:16][C:6]=2[O:5][CH:4]([CH2:3][CH2:2][N:19]2[CH2:20][CH2:21][CH2:22][CH:18]2[CH3:17])[CH2:10]1

참가 물질

6

반응물 4

HCID 11430Potassium CarbonateHCID 130032-MethylpyrrolidineHCID 444972Fumaric AcidHCID 137264422-(chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f]-1,4-oxazepine-5(4H)thione

생성물 1

HCID 14391511(E)-but-2-enedioic acid;4-methyl-2-[2-(2-methylpyrrolidin-1-yl)ethyl]-2,3-dihydropyrido[3,2-f][1,4]oxazepine-5-thione;propan-2-ol수율 32.8%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a suspension of 5.0 g (0.019 mole) of 2-(chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f]-1,4-oxazepine-5(4H)-thione in 25 ml of absolute ethanol was added 3.5 g (0.04 mole) of 2-methylpyrrolidine. The mixture was heated to reflux for 6.5 hr and left standing at room temperature overnight. Mass spec and TLC showed presence of starting materials. Approximately 5 g of potassium carbonate was added and heating at reflux was continued for 24 hr. Ethanol was removed by rotary evaporation (70° C., 30 mm). The residue was taken up in 100 ml of methylene chloride and washed with 2×50 ml dil. aqueous sodium hydroxide. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated by rotary evaporation (70° C., 30 mm). The residual syrup was dissolved in isopropyl aocohol and treated with fumaric acid affording 4.5 g (0.01 mole, 49.2%) of crude crystals. Two recrystallizations from isopropyl afforded 1.5 g (16.4%) of yellow crystals, m.p., 92°-95° C.

후처리

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 6.5 hr
  3. waitleft
  4. temperatureheating
  5. temperatureat reflux
  6. waitwas continued for 24 hr
  7. customEthanol was removed by rotary evaporation (70° C., 30 mm)
  8. washwashed with 2×50 ml dil. aqueous sodium hydroxide
  9. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated by rotary evaporation (70° C., 30 mm)
  12. dissolutionThe residual syrup was dissolved in isopropyl aocohol
  13. customTwo recrystallizations from isopropyl

출처 및 근거

ORD 기록
ord-f80487ff4d8a47d2b5d758272f0f2d59
출처 데이터셋
uspto-grants-1988_02
특허 번호
US04727152

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