m-Chloroperbenzoic acid → HCID 87581588, compound

HRID 2099039Notes

Reaction equation

[C:1]([NH2:5])(=[O:4])[C:2]#[CH:3].[NH2:6][C:7]1[N:11]([C:12]2[C:17]([Cl:18])=[CH:16][C:15]([C:19]([F:22])([F:21])[F:20])=[CH:14][C:13]=2[Cl:23])[N:10]=[C:9]([C:24]([OH:26])=[O:25])[C:8]=1[S:27][C:28]([F:31])([F:30])[F:29].ClC1C=CC=C(C(OO)=[O:40])C=1.S([O-])([O-])=O.[Na+].[Na+].C(=O)([O-])O.[Na+]>ClCCl>[C:1]([NH2:5])(=[O:4])[C:2]#[CH:3].[NH2:6][C:7]1[N:11]([C:12]2[C:13]([Cl:23])=[CH:14][C:15]([C:19]([F:20])([F:21])[F:22])=[CH:16][C:17]=2[Cl:18])[N:10]=[C:9]([C:24]([OH:26])=[O:25])[C:8]=1[S:27]([C:28]([F:31])([F:30])[F:29])=[O:40]

Participants

Conditions

Temperature: 20 °C

Procedure

To a suspension of 5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylthio-I H-pyrazole-3-carboxylic acid propargylamide (0.71 g, 1.43 mmol) in dichloromethane was slowly added a solution of m-chloroperbenzoic acid (70%, 0.41 g, 1.68 mmol) in dichloromethane. After stirring for 17 hours at 20° C., an aqueous solution of sodium sulfite/sodium hydrogen carbonate (5%:5%, 25 ml) was added and stirring continued for 15 minutes. The aqueous phase was extracted with dichloromethane, dried over magnesium sulfate, evaporated and purified by flash chomatography (silica, heptane/ethyl acetate) to give the title compound (0.604 g, yield 86%) as white crystals, mp 207° C., 1H NMR (CDCl3): 2.28 (t, 1H, propargyl), 4.20 (m, 2H, propargyl), 5.17 (bs, 2H, NH2), 6.88 (bt, 1H, C(O)NH), and 7.83 (s, 2H, Ar—H).

Workup

stirringstirring
waitcontinued for 15 minutes
extractionThe aqueous phase was extracted with dichloromethane
dry with materialdried over magnesium sulfate
customevaporated
custompurified by flash chomatography (silica, heptane/ethyl acetate)

Sources & evidence

ORD record: ord-7bd453fc0daf4f3ea55041f1c5a346dd
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07569516B2

Reaction notes

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