Diisopropyl Ether → HCID 14536543, compound

HRID 728705Notes

Reaction equation

HRID 728705 reaction equation
[N:1]1([CH2:8][CH:9]([N:11]2[C:24]3[CH:23]=[C:22]([C:25](=S)[NH:26][CH2:27][CH2:28][CH3:29])[CH:21]=[CH:20][C:19]=3[S:18][C:17]3[C:12]2=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH3:10])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C([O:34]C(C)C)(C)C>C(O)(=O)C>[N:1]1([CH2:8][CH:9]([N:11]2[C:24]3[CH:23]=[C:22]([C:25]([NH:26][CH2:27][CH2:28][CH3:29])=[O:34])[CH:21]=[CH:20][C:19]=3[S:18][C:17]3[C:12]2=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH3:10])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 7914Diisopropyl EtherHCID 14536542HCID 14536542, compound

Product 1

HCID 14536543HCID 14536543, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
20 °C

Procedure

Mercuric aoetate (I.8I g) dissolved in glacial acetic acid (35 cc) is added in the course of 20 minutes to a solution of 10-[(2RS)-1-(perhydro-1-azepinyl)-2-propyl]-N-propyl-2-phenothiazinecarbothioamide (2.5 g) in acetic acid (25 cc), and the mixture is stirred for 45 minutes at a temperature in the region of 20° C. The black suspension obtained is filtered on sintered glass plugged with celite, and the yellow filtrate is concentrated under reduced pressure (30 mm Hg; 4 kPa) at 40° C. The residue is taken up with ethyl acetate (250 cc) and distilled water (50 cc). The organic phase is washed successively with normal sodium hydroxide (2×100 cc) and distilled water (3×100 cc) and with saturated aqueous sodium chloride solution (100 cc) and dried over magnesium sulphate. After filtration, the yellow filtrate is concentrated under reduced pressure (30 mm Hg; 4 kPa) at 40° C. and a crude yellow oil (2.1 g) is thereby obtained This residue is taken up with boiling isopropyl ether (80 cc). The small amount of insoluble matter is removed by filtration and crystallization is primed in the filtrate by cooling maintained with stirring. The crystals are filtered off on sintered glass to give 10-[(2RS)-1-(perhydro-1-azepinyl)-2-propyl]-N-propyl-2-phenothiazinecarboxamide (1.29 g) in the form of an offwhite solid, m.p. 113° C.

Workup

  1. customThe black suspension obtained
  2. filtrationis filtered on sintered glass
  3. concentrationthe yellow filtrate is concentrated under reduced pressure (30 mm Hg; 4 kPa) at 40° C
  4. distillationdistilled water (50 cc)
  5. washThe organic phase is washed successively with normal sodium hydroxide (2×100 cc)
  6. distillationdistilled water (3×100 cc)
  7. dry with materialwith saturated aqueous sodium chloride solution (100 cc) and dried over magnesium sulphate
  8. filtrationAfter filtration
  9. concentrationthe yellow filtrate is concentrated under reduced pressure (30 mm Hg; 4 kPa) at 40° C.
  10. customa crude yellow oil (2.1 g) is thereby obtained This residue
  11. customThe small amount of insoluble matter is removed by filtration and crystallization
  12. temperatureby cooling
  13. temperaturemaintained
  14. stirringwith stirring
  15. filtrationThe crystals are filtered off on sintered glass

Sources & evidence

ORD record
ord-b9bc415461e74120ab89a3696afbf010
Source dataset
uspto-grants-1991_09
Patent number
US05049669

Reaction notes

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