Acetic Acid → 10-[(2RS)-1-diethylamino-2-propyl]-N-(2-methylpropyl)-2-phenothiazinecarboxamide

HRID 728715Notes

Reaction equation

HRID 728715 reaction equation
[CH2:1]([N:3]([CH2:28][CH3:29])[CH2:4][CH:5]([N:7]1[C:20]2[CH:19]=[C:18]([C:21](=S)[NH:22][CH2:23][CH:24]([CH3:26])[CH3:25])[CH:17]=[CH:16][C:15]=2[S:14][C:13]2[C:8]1=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH3:6])[CH3:2].C(O)(=[O:32])C>C(OCC)(=O)C>[CH2:1]([N:3]([CH2:28][CH3:29])[CH2:4][CH:5]([N:7]1[C:20]2[CH:19]=[C:18]([C:21]([NH:22][CH2:23][CH:24]([CH3:26])[CH3:25])=[O:32])[CH:17]=[CH:16][C:15]=2[S:14][C:13]2[C:8]1=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH3:6])[CH3:2]

Participants

4

Reactant 2

HCID 176Acetic Acid2×HCID 1453656710-[(2RS)-1-diethylamino-2-propyl]-N-(2-methylpropyl)-2-phenothiazinecarbothioamide

Product 1

HCID 1453657110-[(2RS)-1-diethylamino-2-propyl]-N-(2-methylpropyl)-2-phenothiazinecarboxamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

A solution of mercuric acetate (0.84 g) in glacial acetic acid (13 cc) is added dropwise during a period of 10 minutes to a solution of 10-[(2RS)-1-diethylamino-2-propyl]-N-(2-methylpropyl)-2-phenothiazinecarbothioamide (1.12 g) in glacial acetic acid (13 cc). The reaction mixture is stirred for 90 minutes at 25° C. and then filtered on sintered glass covered with celite. The celite is washed with acetic acid (2 cc) and the combined filtrates are concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. to give a residue which is then diluted in ethyl acetate (50 cc). The organic phase is washed with normal caustic soda solution (25 cc) and distilled water (3×25 cc) and then with brine (1×25 cc), dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. to give a residue which is purified by chromatography on a column (height: 17.2 cm; diameter: 2.4 cm) of silica gel (0.04-0.06 mm) with a slight excess pressure of nitrogen (40 kPa), eluting with a 50:50 (by volume) mixture (1 liter) of cyclohexane and ethylacetate, collecting 60-cc fractions. Fractions 4 to 14 are combined and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. to give 10-[(2RS)-1-diethylamino-2-propyl]-N-(2-methylpropyl)-2-phenothiazinecarboxamide (0.83 g).

Workup

  1. filtrationfiltered on sintered glass
  2. washThe celite is washed with acetic acid (2 cc)
  3. concentrationthe combined filtrates are concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C.
  4. customto give a residue which
  5. washThe organic phase is washed with normal caustic soda solution (25 cc)
  6. distillationdistilled water (3×25 cc)
  7. dry with materialwith brine (1×25 cc), dried over magnesium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C.
  10. customto give a residue which
  11. customis purified by chromatography on a column (height: 17.2 cm; diameter: 2.4 cm) of silica gel (0.04-0.06 mm) with a slight excess pressure of nitrogen (40 kPa)
  12. washeluting with a 50:50 (by volume) mixture (1 liter) of cyclohexane and ethylacetate
  13. customcollecting 60-cc fractions
  14. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C.

Sources & evidence

ORD record
ord-987f7d422d074e08a20722d0ff84b08c
Source dataset
uspto-grants-1991_09
Patent number
US05049669

Reaction notes

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