Acetic Acid → HCID 14536526, compound

HRID 728699Notes

Reaction equation

HRID 728699 reaction equation
[CH2:1]([N:3]([CH2:26][CH3:27])[CH2:4][CH:5]([N:7]1[C:20]2[CH:19]=[C:18]([C:21](=S)[NH:22][CH2:23][CH3:24])[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:30])C>C(OCC)(=O)C>[CH2:1]([N:3]([CH2:26][CH3:27])[CH2:4][CH:5]([N:7]1[C:20]2[CH:19]=[C:18]([C:21]([NH:22][CH2:23][CH3:24])=[O:30])[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 14536524HCID 14536524, compound

Product 1

HCID 14536526HCID 14536526, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

A solution of mercuric acetate (0.70 g) in acetic acid (11 cc) is added dropwise during a period of 10 minutes to a solution of 10-[(2RS)-1-diethylamino-2-propyl]-N-ethyl-2-phenothiazinecarbothioamide (0.87 g) in glacial acetic acid (11 cc). The reaction mixture is stirred for 90 minutes at 25° C. and then filtered on sintered glass covered with supercel. The celite is washed with acetic acid (2×2 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 diluted in ethyl acetate (50 cc). The organic phase is washed with 1 N sodium hydroxide (20 cc) and distilled water (3×20 cc) and then with brine (1×20 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: 15.5 cm; diameter: 1.6 cm) of alumina (0.05-0.16 mm), eluting with mixtures of cyclohexane and ethyl acetate in proportions (by volume) of 80:20 (375 cc) and 75:25 (3 liters), collecting 25-cc fractions. The first three liters are discarded and fractions 3 to 12 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-ethyl-2-phenothiazinecarboxamide (0.54 g).

Workup

  1. filtrationfiltered on sintered glass
  2. washThe celite is washed with acetic acid (2×2 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 1 N sodium hydroxide (20 cc)
  6. distillationdistilled water (3×20 cc)
  7. dry with materialwith brine (1×20 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: 15.5 cm; diameter: 1.6 cm) of alumina (0.05-0.16 mm)
  12. washeluting with mixtures of cyclohexane and ethyl acetate in proportions (by volume) of 80:20 (375 cc) and 75:25 (3 liters)
  13. customcollecting 25-cc fractions
  14. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C.

Sources & evidence

ORD record
ord-fe97952238e34acb85fbbaecc379c636
Source dataset
uspto-grants-1991_09
Patent number
US05049669

Reaction notes

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