Chloroacetone → HCID 178430839, compound

HRID 704252Notes

Reaction equation

HRID 704252 reaction equation
Cl[CH2:2][C:3](=O)[CH3:4].Cl.[N:7]1([CH2:12][CH:13]([N:15]2[C:28]3[CH:27]=[C:26]([C:29]([NH2:31])=[NH:30])[CH:25]=[CH:24][C:23]=3[S:22][C:21]3[C:16]2=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH3:14])[CH2:11][CH2:10][CH2:9][CH2:8]1>C(O)C.ClCCCl>[CH3:4][C:3]1[N:30]=[C:29]([C:26]2[CH:25]=[CH:24][C:23]3[S:22][C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[N:15]([CH:13]([CH3:14])[CH2:12][N:7]4[CH2:11][CH2:10][CH2:9][CH2:8]4)[C:28]=3[CH:27]=2)[NH:31][CH:2]=1

Participants

5

Reactant 2

HCID 6571ChloroacetoneHCID 14502148HCID 14502148, compound

Product 1

HCID 178430839HCID 178430839, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 702EthanolSolvent

Procedure

Chloroacetone (0.44 cc) and 4 A molecular sieve (1 g) are added to a solution of 10-[(2RS)-1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarboxamidine hydrochloride (1.76 g) in dry ethanol (17 cc). The suspension is maintained under reflux for 20 hours. After cooling, the suspension is filtered and concentrated to dryness at 40° C. under reduced pressure (30 mm Hg; 4 kPa) to give a residue which is diluted in 1,2-dichloroethane (200 cc). The organic phase is washed with distilled water (3×100 cc) and then with saturated sodium chloride solution (100 cc), dried over magnesium sulphate, filtered and concentrated to dryness at 40° C. under reduced pressure (30 mm Hg; 4 kPa) to give a residue which is purified by chromatography on a column (height: 15 cm; diameter: 2.4 cm) of silica (0.04-0.06 mm), eluting with a 90:10 (by volume) mixture (800 cc) of 1,2-dichloroethane and methanol and collecting 50-cc fractions. The first 300 cc of eluate are discarded and fractions 4 to 10 are concentrated to dryness at 40° C. under reduced pressure (30 mm Hg; 4 kPa) to give 2-(4-methyl-2-imidazolyl)-10-[(2RS)-1-(1-pyrrolidinyl)-2-propyl]phenothiazine(0.33g) in the form of a golden yellow solid.

Workup

  1. temperatureThe suspension is maintained
  2. temperatureunder reflux for 20 hours
  3. temperatureAfter cooling
  4. filtrationthe suspension is filtered
  5. concentrationconcentrated to dryness at 40° C. under reduced pressure (30 mm Hg; 4 kPa)
  6. customto give a residue which
  7. washThe organic phase is washed with distilled water (3×100 cc)
  8. dry with materialwith saturated sodium chloride solution (100 cc), dried over magnesium sulphate
  9. filtrationfiltered
  10. concentrationconcentrated to dryness at 40° C. under reduced pressure (30 mm Hg; 4 kPa)
  11. customto give a residue which
  12. customis purified by chromatography on a column (height: 15 cm; diameter: 2.4 cm) of silica (0.04-0.06 mm)
  13. washeluting with a 90:10 (by volume) mixture (800 cc) of 1,2-dichloroethane and methanol
  14. customcollecting 50-cc fractions
  15. concentrationfractions 4 to 10 are concentrated to dryness at 40° C. under reduced pressure (30 mm Hg; 4 kPa)

Sources & evidence

ORD record
ord-4b18cff83fdd489589dfbdaaf468d3b7
Source dataset
uspto-grants-1991_01
Patent number
US04985419

Reaction notes

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