Tetrahydrofuran → HCID 68025181, compound

HRID 76344Notes

Reaction equation

[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8](Cl)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[H-].[Na+].O1[CH:20]=[CH:19][CH2:18][C:17](=[O:21])[NH:16]1.[CH2:22]1[CH2:26][O:25][CH2:24][CH2:23]1>>[CH2:19]([CH:18]1[O:25][C:24]2[C:4]([CH:5]=[CH:6][CH3:7])=[CH:12][CH:26]=[CH:22][C:23]=2[N:16]([C:8]([C:7]2[CH:11]=[CH:12][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)=[O:9])[C:17]1=[O:21])[CH3:20]

Participants

Reactant 4

HCID 8028Tetrahydrofuran

HCID 85024-Nitrobenzoyl chloride

HCID 24758Sodium hydride

HCID 21873527Oxazinone

Product 1

HCID 68025181HCID 68025181, compoundYield 96%

Procedure

Procedure & NMR Data: 107 mg (2.5 eq, 0.58 mmol) of 4-Nitrobenzoyl chloride was added to a mixture of 37 mg (4 eq, 0.92 mmol) of NaH and 50 mg (0.23 mmol) of oxazinone P2 in THF (10 mL). 81 mg of P7 were obtained, yield 96%.

Workup

custom81 mg of P7 were obtained

Sources & evidence

ORD record: ord-de68aadbd1514f7a8c8180039b8ede36
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08835628B2

Reaction notes

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