p-Anisoyl chloride → 2-ethyl-4-(4-methoxyphenylcarbonyl)-8-(prop-1-enyl)-2H-benzo[b][1,4]oxazin-3(4H)-one

HRID 76345Notes

Reaction equation

HRID 76345 reaction equation
[C:1](Cl)(=[O:10])[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[H-].[Na+].O1[CH:19]=[CH:18][CH2:17][C:16](=[O:20])[NH:15]1.[CH2:21]1[CH2:25][O:24][CH2:23][CH2:22]1>>[CH2:18]([CH:17]1[O:24][C:23]2[C:2]([CH:3]=[CH:4][CH3:5])=[CH:1][CH:25]=[CH:21][C:22]=2[N:15]([C:1]([C:2]2[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=2)=[O:10])[C:16]1=[O:20])[CH3:19]

Participants

5

Reactant 4

HCID 7477p-Anisoyl chlorideHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 21873527Oxazinone

Product 1

HCID 897105452-ethyl-4-(4-methoxyphenylcarbonyl)-8-(prop-1-enyl)-2H-benzo[b][1,4]oxazin-3(4H)-oneYield 62%

Procedure

Procedure & NMR Data: 137 mg (2.5 eq, 0.8 mmol) of p-Anisoyl chloride was added to a mixture of 49 mg (4 eq, 1.28 mmol) of NaH and 73 mg (0.32 mmol) of oxazinone P2 in THF (14 mL). 73 mg of P8 were obtained, yield 62%.

Workup

  1. custom73 mg of P8 were obtained

Sources & evidence

ORD record
ord-ef563e10b5ed471cbfbe7b39affab2bb
Source dataset
uspto-grants-2014_09
Patent number
US08835628B2

Reaction notes

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