Hydrochloric Acid → 2-Chloro-1-(10H-phenothiazin-2-yl)ethan-1-one

HRID 1591772Notes

Reaction equation

HRID 1591772 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:18]=[CH:17][C:16]2[S:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8](C(=O)CCl)[C:7]=2[CH:6]=1)=[O:4].[ClH:23]>C(O)(=O)C>[Cl:23][CH2:2][C:3]([C:5]1[CH:18]=[CH:17][C:16]2[S:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[NH:8][C:7]=2[CH:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86108827HCID 86108827, compound

Product 1

HCID 2191812-Chloro-1-(10H-phenothiazin-2-yl)ethan-1-oneYield 82%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2-bromo-1-[10-(chloroacetyl)-10H-phenothiazin-2-yl)ethanone (2.2 g; 5.55 mmol; prepared according to a protocol described in J. Heterocyclic. Chem. (1978), 15, 175, followed by a Friedel-Crafts reaction) is dissolved hot in a mixture of acetic acid (20 ml) and 20% HCl (5.5 ml) and the mixture obtained is heated under reflux for 30 minutes. The reaction mixture is allowed to cool down, the precipitate is filtered, the mixture rinsed with acetic acid (5 ml) and dried under vacuum, the solid obtained is purified by crystallization from toluene in order to produce a brown product with a yield of 82%. Melting point: 190-191° C. (value in the literature: 197-198° C.).

Workup

  1. customprepared
  2. custom(1978), 15, 175, followed by a Friedel-Crafts reaction)
  3. customthe mixture obtained
  4. temperatureis heated
  5. temperatureunder reflux for 30 minutes
  6. temperatureto cool down
  7. filtrationthe precipitate is filtered
  8. washthe mixture rinsed with acetic acid (5 ml)
  9. customdried under vacuum
  10. customthe solid obtained
  11. customis purified by crystallization from toluene in order
  12. customto produce a brown product with a yield of 82%
  13. custom197-198° C.

Sources & evidence

ORD record
ord-c4ce793fb9c84994bfe323f0fe22ee19
Source dataset
uspto-grants-2007_11
Patent number
US07291641B2

Reaction notes

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