Benzenesulfonyl chloride → 2-Benzenesulfonyl-2,9-dihydro-6-oxa-2-azabenzo[cd]azulen-8-one Ethylene Ketal

HRID 25334Notes

Reaction equation

[H-].[Na+].[CH2:3]1[O:19][C:6]2([C:15]3[C:9]4[C:10](=[CH:16][NH:17][CH2:18][C:8]=4[CH2:7]2)[CH:11]=[CH:12][O:13][CH:14]=3)[O:5][CH2:4]1.[C:20]1([S:26](Cl)(=[O:28])=[O:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C)C=O.C(Cl)(Cl)Cl.CCCCCC>[CH2:4]1[O:5][C:6]2([C:15]3[C:9]4[C:10](=[CH:16][N:17]([S:26]([C:20]5[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=5)(=[O:28])=[O:27])[CH2:18][C:8]=4[CH2:7]2)[CH:11]=[CH:12][O:13][CH:14]=3)[O:19][CH2:3]1

Participants

Conditions

Temperature: 60 °C

Procedure

60% Sodium hydride 33 mg was added to a solution of compound (33) in dry dimethylformamide 2 ml with cooling in ice and the mixture was stirred for 10 min. Then, benzenesulfonyl chloride 152 mg was added. The mixture was heated at 60° C. for 14 h. Ice-water was added to the reaction mixtures, which was extracted with ethyl acetate. The extracts were washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue obtained was choromatographed on aluminum oxide in chloroform:hexane (1:1) to give the titled compound (34) as a pale yellow oil, 187 mg. Yield 69%.

Workup

temperaturewith cooling in ice
extractionwas extracted with ethyl acetate
washThe extracts were washed with brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue obtained

Sources & evidence

ORD record: ord-ba1684af748a480b843e644ec5830dbc
Source dataset: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06858640B2

Reaction notes

Loading…