m-Chloroperbenzoic acid → HCID 9839383, compound

HRID 1290807Notes

Reaction equation

ClC1C=CC=C(C(OO)=[O:9])C=1.[CH3:12][S:13][C:14]1[CH:31]=[CH:30][C:17]([O:18][CH:19]([C:21]2[N:26]3[N:27]=[CH:28][N:29]=[C:25]3[N:24]=[CH:23][CH:22]=2)[CH3:20])=[CH:16][CH:15]=1>ClCCl>[CH3:12][S:13]([C:14]1[CH:15]=[CH:16][C:17]([O:18][CH:19]([C:21]2[N:26]3[N:27]=[CH:28][N:29]=[C:25]3[N:24]=[CH:23][CH:22]=2)[CH3:20])=[CH:30][CH:31]=1)=[O:9]

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of 3-chloroperbenzoic acid (0.63 g) in dichloromethane (30 ml) was added dropwise at -78° C. to a stirred solution of 7-{1-[4-(methylthio)phenoxy]ethyl}-1,2,4-triazolo[1,5-a]pyrimidine (0.89 g, prepared in a similar manner to that described in Example 9) in dichloromethane (30 ml). The reaction mixture was stirred at -78° C. for 2 hours, washed with a 10% aqueous solution of sodium hydrogen carbonate followed by water. The organic layer was dried and the solvent was evaporated under reduced pressure. The residue was purified by flash chromatography using as eluent a mixture of dichloromethane and ethanol (in the ratio of 95:5 respectively), followed by recrystallisation from a mixture of ethyl acetate and hexane, to give 7-[1-(4-methylsulphinylphenoxy)ethyl]-1,2,4-triazolo[1,5-a]pyrimidine. Yield 0.76 g, (m.p. 89°-102° C.).

Workup

customprepared in a similar manner to that
washwashed with a 10% aqueous solution of sodium hydrogen carbonate
customThe organic layer was dried
customthe solvent was evaporated under reduced pressure
customThe residue was purified by flash chromatography
additiona mixture of dichloromethane and ethanol (in the ratio of 95:5 respectively),
customfollowed by recrystallisation from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record: ord-fa87478c5f92488db982e96dc48bdefd
Source dataset: uspto-grants-1998_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05753665

Reaction notes

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