Imidazole → Phenoxazine

HRID 2395124Notes

Reaction equation

HRID 2395124 reaction equation
[Si](Cl)(C(C)(C)C)(C)C.C(O[C:12]1[CH:13]=[CH:14][C:15]2[N:20](CC)[C:19]3[CH:23]=[CH:24][C:25](OCC)=[CH:26][C:18]=3[O:17][C:16]=2[C:30]=1CO)C.N1C=CN=C1.O>CN(C)C=O.CCCCCC.C(OCC)C>[CH:23]1[C:19]2[NH:20][C:15]3[CH:14]=[CH:13][CH:12]=[CH:30][C:16]=3[O:17][C:18]=2[CH:26]=[CH:25][CH:24]=1

Participants

8

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 18972576HCID 18972576, compound

Product 1

HCID 67278Phenoxazine

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent2×HCID 8058HexaneSolvent

Procedure

A solution of 1.92 g (1.3 eq.) of tert-butyldimethylsilyl chloride in 10 ml of N,N-dimethylformamide was added dropwise while cooling with ice to a mixture of 3.23 g (9.80 mmol) of 3,7-diethoxy-10-ethyl-10H-dibenzo[b,e][1,4]oxazine-4-methanol and 1.47 g (2.2 eq.) of imidazole in 30 ml of N,N-dimethylformamide. The reaction mixture was stirred at 0° for 30 minutes, brought slowly to room temperature, stirred for 1 hour and then poured into 100 ml of water, 50 ml of diethyl ether and 50 ml of hexane. The organic phase was separated, extracted twice with water, dried over magnesium sulphate and concentrated. The residue was chromatographed on 250 g of silica gel with diethyl ether/hexane (1:10), whereupon, after drying in a high vacuum, 4.30 g (98.9%) of 10-methyl-3,7-diethoxyl-4-[(tert-butyl-dimethylsilyl)oxy]methyl!-10H-dibenzo[b,e][1,4]oxazine were obtained as a colourless solid of m.p. 77.5°-78.5°.

Workup

  1. custombrought slowly to room temperature
  2. stirringstirred for 1 hour
  3. customThe organic phase was separated
  4. extractionextracted twice with water
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated
  7. customThe residue was chromatographed on 250 g of silica gel with diethyl ether/hexane (1:10), whereupon
  8. customafter drying in a high vacuum, 4.30 g (98.9%) of 10-methyl-3,7-diethoxyl-4-[(tert-butyl-dimethylsilyl)oxy]methyl

Sources & evidence

ORD record
ord-38c402d4becc47e196727cf00f6ec235
Source dataset
uspto-grants-1998_09
Patent number
US05811389

Reaction notes

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