Toluene → 10-Ethyl-10H-phenoxazine-3,7-dicarbaldehyde

HRID 2287299Notes

Reaction equation

HRID 2287299 reaction equation
C([N:3]1[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:10][C:9]2[C:4]1=CC=CC=2)C.CN([CH:20]=[O:21])C.P(Cl)(Cl)(Cl)=[O:23].[C:27]1([CH3:33])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>[Cl-].[Zn+2].[Cl-]>[CH:33]([C:27]1[CH:32]=[CH:31][C:30]2[N:3]([CH2:4][CH3:9])[C:16]3[C:11]([O:10][C:29]=2[CH:28]=1)=[CH:12][C:13]([CH:20]=[O:21])=[CH:14][CH:15]=3)=[O:23]

Participants

6

Reactant 4

HCID 1140TolueneHCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 328622710-ethylphenoxazine

Product 1

HCID 1870448110-Ethyl-10H-phenoxazine-3,7-dicarbaldehyde

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

Reaction was conducted using 2.7 g (12.8 mmol) of 10-ethylphenoxazine (4c), 3.8 g (52.0 mmol) of DMF, 1.8 g (13.2 mmol) of zinc chloride, 7.8 g (50.9 mmol) of phosphorus oxychloride, and 50 ml of toluene in the same manner as in Example 1 (2). The resultant reaction mixture was treated in the same manner to obtain 2.47 g of 3,7-diformyl-10-ethylphenoxazine (2c). Yield, 72.3%; m.p., 199-200° C.

Workup

  1. customReaction
  2. customThe resultant reaction mixture
  3. additionwas treated in the same manner

Sources & evidence

ORD record
ord-b441abee16394c7b844aba2a481ac493
Source dataset
uspto-grants-2000_07
Patent number
US06083651

Reaction notes

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