Diethylamine → 7-Chloro-2-[2-(diethylamino)ethyl]-2,3-dihydro-4-methylpyrido[3,2-f][1,4]-oxazepin-5(4H)-one oxalate

HRID 364440

반응식

HRID 364440 반응식
[Cl:1][C:2]1[CH:12]=[N:11][C:10]2[O:9][CH:8]([CH2:13][CH2:14]Cl)[CH2:7][N:6]([CH3:16])[C:5](=[O:17])[C:4]=2[CH:3]=1.[CH2:18]([NH:20][CH2:21][CH3:22])[CH3:19].C([O:25][C:26](=[O:28])C)C.[CH3:29][OH:30].[OH-:31].[NH4+]>C(O)C>[C:26]([OH:28])(=[O:25])[C:29]([OH:31])=[O:30].[Cl:1][C:2]1[CH:12]=[N:11][C:10]2[O:9][CH:8]([CH2:13][CH2:14][N:20]([CH2:21][CH3:22])[CH2:18][CH3:19])[CH2:7][N:6]([CH3:16])[C:5](=[O:17])[C:4]=2[CH:3]=1

참가 물질

6

반응물 4

HCID 8021Diethylamine3회HCID 14923Ammonium HydroxideHCID 137264457-Chloro-2-(2-chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f][1,4]oxazepin-5(4H)-oneHCID 21584119Ethylacetate methanol

생성물 1

HCID 137265987-Chloro-2-[2-(diethylamino)ethyl]-2,3-dihydro-4-methylpyrido[3,2-f][1,4]-oxazepin-5(4H)-one oxalate수율 76%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a suspension of 7-chloro-2-(2-chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f][1,4]oxazepine-5(4H)-one in 50 ml of absolute ethanol was added 2.26 ml (0.022 mole) of diethylamine and the mixture heated to reflux. (Complete dissolution occurred). After 1 hr, another 2.26 ml (0.022 mole) of diethylamine was added followed by 5.0 ml (0.049 mole) and heating continued for 2 more hours. TLC (ethylacetate/methanol/conc. ammonium hydroxide, 7:2:1, v/v/v) still showed presence of starting material; another 2.26 ml (0.022 mole) of diethylamine was added and heating continued for 15 hr at reflux. Solvent was removed by rotary evaporation (60° C., 30 mm Hg) and the residue taken up in methylene chloride, washed twice with dilute aqueous sodium hydroxide and once with water. The organic layer was dried over sodium sulfate, filtered and concentrated by rotary evaporation, and azeotroped once with toluene. The oil was treated with oxalic acid in isopropyl alcohol which yielded 6.7 g (76%) of white crystals, m.p. 163°-164° C.

후처리

  1. temperaturethe mixture heated to reflux
  2. dissolution(Complete dissolution occurred)
  3. temperatureheating
  4. temperatureheating
  5. waitcontinued for 15 hr
  6. temperatureat reflux
  7. customSolvent was removed by rotary evaporation (60° C., 30 mm Hg)
  8. washwashed twice with dilute aqueous sodium hydroxide and once with water
  9. dry with materialThe organic layer was dried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated by rotary evaporation
  12. customazeotroped once with toluene
  13. additionThe oil was treated with oxalic acid in isopropyl alcohol which

출처 및 근거

ORD 기록
ord-d0fa3021b96848f5a2cdba8f47c347a5
출처 데이터셋
uspto-grants-1986_08
특허 번호
US04604388

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