Ethyl 3,4-dihydro-2H-1,4-benzoxazine-2-carboxylate → HCID 10948640, compound

HRID 1106467Notes

Reaction equation

HRID 1106467 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][NH:10][C:9]2[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=2[O:7]1)=[O:5])[CH3:2].[C:16]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=[O:19])[CH:17]=[CH2:18]>O.C1(C)C=CC=CC=1>[CH2:21]([O:20][C:16]([CH2:17][CH2:18][N:10]1[C:9]2[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=2[O:7][CH:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:11]1)=[O:19])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 2

HCID 31090Ethyl 3,4-dihydro-2H-1,4-benzoxazine-2-carboxylateHCID 75617Benzyl acrylate

Product 1

HCID 10948640HCID 10948640, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

2.3 mmol (0.9 ml) of 40% Triton B in water are added at 0° C. to 22.6 mmol (5 g) of 2-ethoxycarbonyl-3,4-dihydro-2H-1,4-benzoxazine (described in J. Heterocyclic Chem., 1985, 22, 177) and 79 mmol (12.8 g) of benzyl acrylate in 17 ml of toluene. The reaction mixture is refluxed overnight, the solvent is evaporated off and the reaction mixture is heated again for 24 hours. After cooling, hydrolysis and extraction with ethyl acetate, the organic phase is concentrated and purified by chromatography on silica gel using an ethyl acetate/petroleum ether mixture (3/7) as eluant to yield the expected compound.

Workup

  1. temperatureThe reaction mixture is refluxed overnight
  2. customthe solvent is evaporated off
  3. temperaturethe reaction mixture is heated again for 24 hours
  4. temperatureAfter cooling
  5. customhydrolysis and extraction with ethyl acetate
  6. concentrationthe organic phase is concentrated
  7. custompurified by chromatography on silica gel using an ethyl acetate/petroleum ether mixture (3/7) as eluant

Sources & evidence

ORD record
ord-614e7c13452d42f89898e4bf82d1b80a
Source dataset
uspto-grants-2000_05
Patent number
US06057317

Reaction notes

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