Iodoethane → 10-ethylphenoxazine

HRID 1586288Notes

Reaction equation

HRID 1586288 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.

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-abe2815eef714fcaade5117f81ac6d2d
Source dataset
uspto-grants-1999_08
Patent number
US05942615

Reaction notes

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