Acetic Acid → HCID 86745076, compound

HRID 728733Notes

Reaction equation

HRID 728733 reaction equation
[ClH:1].CC(C)CCC[NH:7][C:8]([C:10]1[CH:23]=[CH:22][C:21]2[S:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13](C(C)CN3CCCC3)[C:12]=2[CH:11]=1)=S.C(O)(=[O:35])C>O>[ClH:1].[CH:11]1[C:12]2[NH:13][C:14]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[S:20][C:21]=2[CH:22]=[CH:23][C:10]=1[C:8]([NH2:7])=[O:35]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 14536624HCID 14536624, compound

Product 1

HCID 86745076HCID 86745076, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of N-(4-methylpentyl)-l0-[(2RS)-1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarbothioamide hydrochloride (1.2 g) and mercuric acetate (0.88 g) in acetic acid (20.5 cc) is stirred for 16 hours at a temperature in the region of 20° C. The orange suspension obtained is diluted with distilled water (50 cc), filtered and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. The residue is taken up with distilled water (50 cc) and ethyl acetate (100 cc). The mixture is alkalinized to pH 13 with sodium hydroxide (d=1.33). The organic phase is separated and then washed successively with distilled water (2×25 cc) and saturated aqueous sodium chloride solution (25 cc). The organic phase is then dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. The oily yellow residue (0.82 g) is dissolved in ethyl acetate (10 cc) and treated, with stirring, with a 3.3N solution (0.55 cc) of hydrochloric acid in isopropyl ether. After 1 hour with stirring at a temperature in the region of 5° C., the solid formed is drained, washed with ethyl ether (3×10 cc) and dried under reduced pressure (5 mm Hg; 0.7 kPa) at 40° C. N-(4-Metylpentyl)-l0-[(2RS)-1-1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarboxamide hydrochloride (0.6 g) is thereby obtained in the form of a very pale yellow solid, m.p. 218° C.

Workup

  1. customThe orange suspension obtained
  2. filtrationfiltered
  3. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C
  4. customThe organic phase is separated
  5. washwashed successively with distilled water (2×25 cc) and saturated aqueous sodium chloride solution (25 cc)
  6. dry with materialThe organic phase is then dried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C
  9. dissolutionThe oily yellow residue (0.82 g) is dissolved in ethyl acetate (10 cc)
  10. additiontreated
  11. stirringwith stirring, with a 3.3N solution (0.55 cc) of hydrochloric acid in isopropyl ether
  12. stirringAfter 1 hour with stirring at a temperature in the region of 5° C.
  13. customthe solid formed
  14. washwashed with ethyl ether (3×10 cc)
  15. customdried under reduced pressure (5 mm Hg; 0.7 kPa) at 40° C

Sources & evidence

ORD record
ord-88c635fbd72b43369cbd1f0b8a8b7f75
Source dataset
uspto-grants-1991_09
Patent number
US05049669

Reaction notes

Loading…