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

HRID 76342Notes

Reaction equation

[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].O1[CH:17]=[CH:16][CH2:15][C:14](=[O:18])[NH:13]1.[CH2:19]1[CH2:23][O:22][CH2:21][CH2:20]1>>[CH2:16]([CH:15]1[O:22][C:21]2[C:2]([CH:3]=[CH:4][CH3:5])=[CH:1][CH:23]=[CH:19][C:20]=2[N:13]([C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:8])[C:14]1=[O:18])[CH3:17]

Participants

Reactant 4

HCID 7412Benzoyl chloride

HCID 8028Tetrahydrofuran

HCID 24758Sodium hydride

HCID 21873527Oxazinone

Product 1

HCID 773903382-ethyl-4-(phenylcarbonyl)-8-(prop-1-enyl)-2H-benzo[b][1,4]oxazin-3(4H)-oneYield 77%

Procedure

Procedure & NMR Data: 142 μL (2.5 eq, 1.23 mmol) of benzoyl chloride was added to a mixture of 78 mg of NaH (4 eq, 1.96 mmol) and 100 mg (0.49 mmol) of oxazinone P2 in THF (9.5 ml). 58 mg of P4 were obtained, yield 77%.

Workup

custom58 mg of P4 were obtained

Sources & evidence

ORD record: ord-7c9777b490be4e7ca100fa14a6e8f3b7
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08835628B2

Reaction notes

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