Acetyl chloride → 1,1'-(10H-Phenothiazine-2,10-diyl)bisethan-1-one

HRID 131098Notes

Reaction equation

HRID 131098 reaction equation
[C:1]([C:4]1[CH:17]=[CH:16][C:15]2[S:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]=2[CH:5]=1)(=[O:3])[CH3:2].[C:18](Cl)(=[O:20])[CH3:19]>C1(C)C=CC=CC=1>[C:18]([N:7]1[C:6]2[CH:5]=[C:4]([C:1](=[O:3])[CH3:2])[CH:17]=[CH:16][C:15]=2[S:14][C:13]2[C:8]1=[CH:9][CH:10]=[CH:11][CH:12]=2)(=[O:20])[CH3:19]

Participants

4

Reactant 2

HCID 6367Acetyl chloride2×HCID 81131Methyl phenothiazin-2-yl ketone

Product 1

HCID 811321,1'-(10H-Phenothiazine-2,10-diyl)bisethan-1-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

30 g (0.118 mol) of 2-acetylphenothiazine and 9.28 g (1 eq.) of acetyl chloride are introduced into a 500 ml flask containing 150 ml of toluene. The reaction mixture is heated to reflux for 45 minutes before the introduction of a new portion of 4.6 g (0.5 eq.) of acetyl chloride. Stirring is maintained under heating at reflux for another 2 hours. The reaction medium is then poured onto approximately 200 g of ice. After stirring, the organic phase is decanted and washed successively with 100 ml of water and 100 ml of salt water. The organic solution is dried over sodium sulphate, filtered and concentrated to dryness using a rotary evaporator. A yellow solid (33 g; 100%) is obtained which is used in the following stage without additional purification.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureis maintained
  3. temperatureunder heating
  4. temperatureat reflux for another 2 hours
  5. stirringAfter stirring
  6. customthe organic phase is decanted
  7. washwashed successively with 100 ml of water and 100 ml of salt water
  8. dry with materialThe organic solution is dried over sodium sulphate
  9. filtrationfiltered
  10. concentrationconcentrated to dryness
  11. customa rotary evaporator
  12. customA yellow solid (33 g; 100%) is obtained which
  13. customis used in the following stage without additional purification

Sources & evidence

ORD record
ord-ce0b6e13712540738b6de28933b6a917
Source dataset
uspto-grants-2008_06
Patent number
US07384933B2

Reaction notes

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