Iodoethane → N-Ethylphenothiazine

HRID 6577

Reaction equation

HRID 6577 reaction equation
[CH:1]1[C:14]2[NH:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[S:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.I[CH2:16][CH3:17].[OH-].[K+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH2:16]([N:13]1[C:14]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=2[S:6][C:7]2[C:12]1=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH3:17]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 7108PhenothiazineHCID 14797Potassium Hydroxide

Product 1

HCID 219178N-Ethylphenothiazine

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 10 g (0.05 mol) of phenothiazine, 11.7 g (0.075 mol) of iodoethane, 4.2 g (0.075 mol) of potassium hydroxide and 0.25 g of tetra-n-butylammonium hydrogen sulfate in 200 ml of dry toluene was refluxed for 24 hours. After cooling, the reaction mixture was filtered, and the solvent was evaporated. The product was crystallized from methanol. The yield of 10-ethylphenothiazine (C14H13NS, FW=227.33) was 90%.

Workup

  1. temperaturewas refluxed for 24 hours
  2. temperatureAfter cooling
  3. filtrationthe reaction mixture was filtered
  4. customthe solvent was evaporated
  5. customThe product was crystallized from methanol

Sources & evidence

ORD record
ord-625c6e1d30dd4d0a9f0e4279bcd0f5ff
Source dataset
uspto-grants-2006_08
Patent number
US07083884B2

Linked notes

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