Benzenesulfonic Acid → (S)-Zopiclone Besylate

HRID 217646

Reaction equation

[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C@@H:11]2[N:20]([C:21]3[CH:22]=[CH:23][C:24]([Cl:27])=[CH:25][N:26]=3)[C:18](=[O:19])[C:13]3[N:14]=[CH:15][CH:16]=[N:17][C:12]2=3)=[O:9])[CH2:4][CH2:3]1.[C:28]1([S:34]([OH:37])(=[O:36])=[O:35])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C(O)C>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C@@H:11]2[N:20]([C:21]3[CH:22]=[CH:23][C:24]([Cl:27])=[CH:25][N:26]=3)[C:18](=[O:19])[C:13]3[N:14]=[CH:15][CH:16]=[N:17][C:12]2=3)=[O:9])[CH2:4][CH2:3]1.[S:34]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([O-:37])(=[O:36])=[O:35]

Participants

Conditions

Temperature: 0 °C

Procedure

A reactor was charged with 0.123 g (S)-zopiclone. To the reactor was added 0.056 g benzenesulfonic acid. The reaction was agitated and charged with 17.2 g ethanol. The reaction was cooled to 0° C., and the reaction was allowed to stir for greater than one hour after a slurry appeared. The reaction mixture was filtered and washed once with 0.5 g ethanol, dried in vacuo at approximately 50° C. for approximately 6 h to yield the titled compound in 52% yield.

Workup

stirringto stir for greater than one hour after a slurry
filtrationThe reaction mixture was filtered
washwashed once with 0.5 g ethanol
customdried in vacuo at approximately 50° C. for approximately 6 h

Sources & evidence

ORD record: ord-800d98d95cfe40568d76bfcb4c6ca8c5
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08198278B2

Linked notes

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