Ethyl 4-bromocrotonate → Ethyl 3,4-dihydro-2H-1,4-benzoxazine-3-acetate

HRID 1078557Notes

Reaction equation

HRID 1078557 reaction equation
[Na].[OH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9]C(=O)C(F)(F)F.Br[CH2:17][CH:18]=[CH:19][C:20]([O:22][CH2:23][CH3:24])=[O:21]>C(O)C>[O:2]1[C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[NH:9][CH:18]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:17]1

Participants

5

Reactant 3

HCID 98102Ethyl 4-bromocrotonateHCID 5360545SodiumHCID 132784972,2,2-trifluoro-N-(2-hydroxyphenyl)acetamide

Product 1

HCID 10632771Ethyl 3,4-dihydro-2H-1,4-benzoxazine-3-acetate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

650 ml of ethanol are introduced into a 3 l reactor, with magnetic stirring, cooled to 0° C., 5.9 g (0.259 mol) of sodium are added slowly, in small portions, followed by successive dropwise addition of 53 g (0.259 mol) of N-(2-hydroxyphenyl)trifluoroacetamide and 50 g (0.259 mol) of 75% pure ethyl 4-bromo-2-butenoate, and the mixture is heated at 80° C. for 1.5 h.

Workup

  1. temperaturethe mixture is heated at 80° C. for 1.5 h.

Sources & evidence

ORD record
ord-e248054094164b0885e21f23e5b4ed2d
Source dataset
uspto-grants-1996_08
Patent number
US05550125

Reaction notes

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