(Phenylthio)acetyl chloride → 2-(5-Phenylsulfanylmethyl-[1,2,4]oxadiazol-3-ylmethyl)-isoindole-1,3-dione

HRID 602784Notes

Reaction equation

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

Participants

Conditions

Temperature: 105 °C

Procedure

To 10 g (0.046 mol) of 2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-N-hydroxy-acetamidine dissolved in 500 mL of DMF, 1.84 g (0.046 mol, 1 eq) of magnesium oxide were added. After 15 min, 8.5 g (0.046 mol, 1 eq) of phenylsulfanyl-acetyl chloride were added, and the temperature was raised to 105° C. and the solution was stirred overnight. The reaction mixture was partitioned between aqueous NH4Cl and EtOAc, dried over Na2SO4. Column chromatography on silica gel with EtOAc/Heptane 1:1 yielded 8.7 g (55%) of 2-(5-phenylsulfanylmethyl-[1,2,4]oxadiazol-3-ylmethyl)-isoindole-1,3-dione as a light yellow solid, MS: 352 (MH+).

Workup

customThe reaction mixture was partitioned between aqueous NH4Cl and EtOAc
dry with materialdried over Na2SO4

Sources & evidence

ORD record: ord-1791bd9f30f5405e9ed12265a8df7937
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07906546B2

Reaction notes

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