Thionyl Chloride → 1-(phenylsulfonyl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine-7-carbonyl chloride

HRID 2421890Notes

Reaction equation

[C:1]1([S:7]([N:10]2[CH2:15][CH2:14][O:13][C:12]3[N:16]=[CH:17][C:18]([C:20]([OH:22])=O)=[CH:19][C:11]2=3)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)([Cl:25])=O>ClCCCl>[C:1]1([S:7]([N:10]2[CH2:15][CH2:14][O:13][C:12]3[N:16]=[CH:17][C:18]([C:20]([Cl:25])=[O:22])=[CH:19][C:11]2=3)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 1-(phenylsulfonyl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine-7-carboxylic acid (230 mg, 0.718 mmol) in DCE (20 mL) was added thionyl chloride (0.5 mL, 6.85 mmol). The solution turned cloudy white. The reaction was heated to 70° C. and stirred at that temperature for 2 hours, after which time the solution was clear. LCMS analysis of the reaction mixture indicated consumption of starting material. The reaction mixture was concentrated in vacuo. 1-(phenylsulfonyl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine-7-carbonyl chloride (243 mg, 0.718 mmol, 100% yield) was used without purification. LCMS (methanol adduct, i.e. the methyl ester; +ESI) m/z=335.0 [M+H]+.

Workup

customconsumption of starting material
concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record: ord-b86ce7d8e7204c439539ad84b3bb24af
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07960377B2

Reaction notes

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