Tetrahydrofuran → HCID 24893993, compound

HRID 746746Notes

Reaction equation

ClC(Cl)(O[C:5](=[O:11])[O:6][C:7](Cl)(Cl)Cl)Cl.[NH2:13][C:14]1[CH:19]=[CH:18][C:17]([S:20]([NH:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[C:30](=[O:37])[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)(=[O:22])=[O:21])=[CH:16][CH:15]=1.[CH2:38]1[CH2:42][O:41][CH2:40][CH2:39]1>C(N(CC)CC)C>[C:30]([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[NH:23][S:20]([C:17]1[CH:16]=[CH:15][C:14]([NH:13][C:5](=[O:11])[O:6][CH2:7][CH:40]2[CH2:39][CH2:38][CH2:42][O:41]2)=[CH:19][CH:18]=1)(=[O:22])=[O:21])(=[O:37])[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Triphosgene (28 mg, 1/3 equiv) was dissolved in 1 mL of THF and the solution cooled to 0° C. A solution of 4-amino-N-(2-benzoylphenyl)benzenesulfonamide (100 mg) in 3 mL of THF and 0.15 mL of triethylamine was added therto, and the reaction mixture was warmed to rt and stirred for 30 minutes. A solution of tetrahyhdrofurfuryl alcohol (44 mg, 1.5 equiv) in 3 mL of THF and 0.15 mL of triethylamine was added thereto and the reaction mixture was left stirring overnight. The reaction was quenched with water and diluted with EtOAc. The organic layer was washed once each with water and brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The title product was obtained following flash chromatography (10% to 95% EtOAc/hexanes). ESMS, M+H+ found: 481.8.

Workup

temperaturewas warmed to rt
waitthe reaction mixture was left
stirringstirring overnight
customThe reaction was quenched with water
additiondiluted with EtOAc
washThe organic layer was washed once each with water and brine
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-d0db8c8263cb43b486ab5a2f1e9e67ce
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07393873B2

Reaction notes

Loading…