Iodoethane → 10-ethylphenoxazine

HRID 2287298Notes

Reaction equation

HRID 2287298 reaction equation
[CH:1]1[C:14]2[NH:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[O: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[O:6][C:7]2[C:12]1=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH3:24]

Participants

7

Reactant 4

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 67278Phenoxazine2×

Product 1

HCID 328622710-ethylphenoxazineYield 78.5%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 1140TolueneSolvent2×

Procedure

Into a reaction flask were introduced 3.0 g (16.4 mmol) of phenoxazine, 6.5 g (98.5 mmol) of 85% KOH, 3.7 g (26.8 mmol) of potassium carbonate, 577 mg (1.7 mmol) of tetra-n-butylammonium hydrogensulfate, and 100 ml of toluene. Thereto was gradually added 5.1 g (32.7 mmol) of ethyl iodide with a dropping funnel (slight heat generation occurred). Subsequently, the mixture was reacted at 60 to 80° C. for 7 hours. After the disappearance of the phenoxazine was ascertained by TLC and gas chromatography, the resultant toluene solution was cooled, washed with water three times, dried (with MgSO4), and then concentrated. The residue was distilled under vacuum to obtain 2.72 g of 10-ethylphenoxazine. Yield, 78.7%; b.p., 120-122° C./1 mmHg.

Workup

  1. customSubsequently, the mixture was reacted at 60 to 80° C. for 7 hours
  2. washwashed with water three times
  3. dry with materialdried (with MgSO4)
  4. concentrationconcentrated
  5. distillationThe residue was distilled under vacuum

Sources & evidence

ORD record
ord-33984304e15049f9a7fb694aa957f065
Source dataset
uspto-grants-2000_07
Patent number
US06083651

Reaction notes

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