Iodoethane → N-Ethylphenothiazine

HRID 2287291Notes

Reaction equation

HRID 2287291 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.[OH-].[K+].C(=O)([O-])[O-].[K+].[K+].[CH2:23](I)[CH3:24]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH2:23]([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)[CH3:24]

Participants

7

Reactant 4

HCID 6340IodoethaneHCID 7108PhenothiazineHCID 11430Potassium CarbonateHCID 14797Potassium Hydroxide

Product 1

HCID 219178N-EthylphenothiazineYield 83.8%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 1140TolueneSolvent

Procedure

Into a 1-liter reaction flask were introduced 25 g (0.126 mol) of phenothiazine, 50.0 g (0.757 mol) of 85% KOH, 4.3 g (0.013 mol) of tetra-n-butylammonium hydrogensulfate, 28.0 g (0.203 mol) of potassium carbonate, and 500 ml of toluene. Thereto was gradually added 39.0 g (0.250 mol) of ethyl iodide. The mixture was reacted at 60 to 70° C. for 5 hours and then filtered. The filtrate was washed twice with water, dried with magnesium sulfate, and then concentrated. As a result, 28.7 g of a crude reaction product was obtained. This crude product was recrystallized from 100 ml of isopropanol to obtain 23.99 g of 10-ethylphenothiazine (4a).

Workup

  1. customInto a 1-liter reaction flask
  2. customThe mixture was reacted at 60 to 70° C. for 5 hours
  3. filtrationfiltered
  4. washThe filtrate was washed twice with water
  5. dry with materialdried with magnesium sulfate
  6. concentrationconcentrated
  7. customAs a result, 28.7 g of a crude reaction product
  8. customwas obtained
  9. customThis crude product was recrystallized from 100 ml of isopropanol

Sources & evidence

ORD record
ord-9f1cf32c91884cd99d2b869f5f8eb256
Source dataset
uspto-grants-2000_07
Patent number
US06083651

Reaction notes

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