Chlorosulfonic acid → HCID 20227234, compound

HRID 1731816Notes

Reaction equation

[F:1][C:2]1[C:3]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:4]2[O:9][CH2:8][CH:7]([CH3:10])[N:6]3[CH:11]=[C:12]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:13](=[O:16])[C:14]([CH:15]=1)=[C:5]23.[Cl:28][S:29](O)(=[O:31])=[O:30]>ClCCl>[F:1][C:2]1[C:3]([C:22]2[CH:27]=[CH:26][C:25]([S:29]([Cl:28])(=[O:31])=[O:30])=[CH:24][CH:23]=2)=[C:4]2[O:9][CH2:8][CH:7]([CH3:10])[N:6]3[CH:11]=[C:12]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:13](=[O:16])[C:14]([CH:15]=1)=[C:5]23

Participants

Conditions

Temperature: 0 °C

Procedure

A suspension of ethyl 9-fluoro-10-phenyl-3-methyl-7-oxo-2,3-dihydro-(7H)-pyrido-(1,2,3-de)-1,4-benzoxazine-6-carboxylate (0.4 g, 1.2 mmol) in dichloromethane (15 ml) was cooled to 0° C. with stirring. Chlorosulfonic acid (5 ml) was added dropwise over 5 minutes. The dark solution was stirred at 0° C. for 15 minutes, then it was warmed gradually to room temperature over 1.5 hour. The reaction mixture was poured onto ice water with stirring. Three extractions with chloroform, drying the combined organic layers over magnesium sulfate, filtration and removal of solvent in vacuo gave a yellow oil (0.5 g) which was used without further purification.

Workup

stirringThe dark solution was stirred at 0° C. for 15 minutes
temperatureit was warmed gradually to room temperature over 1.5 hour
additionThe reaction mixture was poured onto ice water
stirringwith stirring
extractionThree extractions with chloroform
customdrying the combined organic layers
filtrationover magnesium sulfate, filtration and removal of solvent in vacuo

Sources & evidence

ORD record: ord-f0c6549b35554f0e86db749850da3210
Source dataset: uspto-grants-1986_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04623650

Reaction notes

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