Oxalic Acid → 2-[2-[[[4-(1,1-Dimethylethyl)phenyl]methyl]methylamino]ethyl]-2,3-dihydro-4-methylpyrido[3,2-f]-1,4-oxazepine-5 (4H)-thione oxalate

HRID 247345

반응식

HRID 247345 반응식
[CH3:1][N:2]1[C:8](=[S:9])[C:7]2[CH:10]=[CH:11][CH:12]=[N:13][C:6]=2[O:5][CH:4]([CH2:14][CH2:15][NH:16][CH3:17])[CH2:3]1.C(N(C(C)C)CC)(C)C.[C:27]([C:31]1[CH:38]=[CH:37][C:34]([CH2:35]Cl)=[CH:33][CH:32]=1)([CH3:30])([CH3:29])[CH3:28].[C:39]([OH:44])(=[O:43])[C:40]([OH:42])=[O:41]>C(O)(C)C.C(O)C>[C:39]([OH:44])(=[O:43])[C:40]([OH:42])=[O:41].[CH3:28][C:27]([C:31]1[CH:38]=[CH:37][C:34]([CH2:35][N:16]([CH3:17])[CH2:15][CH2:14][CH:4]2[CH2:3][N:2]([CH3:1])[C:8](=[S:9])[C:7]3[CH:10]=[CH:11][CH:12]=[N:13][C:6]=3[O:5]2)=[CH:33][CH:32]=1)([CH3:30])[CH3:29]

참가 물질

7

반응물 4

HCID 971Oxalic AcidHCID 81531DiisopropylethylamineHCID 88198Benzene, 1-(chloromethyl)-4-(1,1-dimethylethyl)-HCID 137265252,3-dihydro-4-methyl-2-[2-(methylamino)ethyl]pyrido[3,2-f]-1,4-oxazepine-5(4H)-thione

생성물 1

HCID 212714622-[2-[[[4-(1,1-Dimethylethyl)phenyl]methyl]methylamino]ethyl]-2,3-dihydro-4-methylpyrido[3,2-f]-1,4-oxazepine-5 (4H)-thione oxalate

시약·촉매·용매 2

HCID 702Ethanol용매HCID 3776Isopropanol용매

실험 절차

To 40 ml of absolute ethanol was added 6.6 g of 2,3-dihydro-4-methyl-2-[2-(methylamino)ethyl]pyrido[3,2-f]-1,4-oxazepine-5(4H)-thione and 3.35 g (0.026 mole) of diisopropylethylamine. While stirring, 4.75 g (0.026 mole) of p-(t-butyl)benzyl chloride was added at a rapid drop rate. The reaction solution was heated to reflux for 4 hr. After cooling, ethanol was removed by rotary evaporation. The residue was taken up in 100 ml of methylene chloride and the solution was washed with 2×50 ml of 1N potassium hydroxide and 50 ml of water, dried over sodium sulfate, and filtered. The methylene chloride was removed by rotary evaporation and ethylacetate was added to the residue which caused some precipitate to fall out (probably quaternary). After filtering off the precipitate, ethyl acetate was removed by rotary evaporation. The oily residue was heated with 2 equivalents of oxalic acid in isopropyl alcohol which yielded 4.3 g (31%) of yellow, analytically pure crystals, m.p. 175° -78° C.

후처리

  1. temperatureThe reaction solution was heated
  2. temperatureto reflux for 4 hr
  3. temperatureAfter cooling
  4. customethanol was removed by rotary evaporation
  5. washthe solution was washed with 2×50 ml of 1N potassium hydroxide and 50 ml of water
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customThe methylene chloride was removed by rotary evaporation and ethylacetate
  9. additionwas added to the residue which
  10. filtrationAfter filtering off the precipitate, ethyl acetate
  11. customwas removed by rotary evaporation
  12. customyielded 4.3 g (31%) of yellow, analytically pure crystals, m.p. 175° -78° C.

출처 및 근거

ORD 기록
ord-27df78cd384b411d892549aa5e3ba09a
출처 데이터셋
uspto-grants-1987_11
특허 번호
US04705853

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