m-Chloroperbenzoic acid → HCID 178527108, compound

HRID 847136Notes

Reaction equation

[C:1]1([CH2:7][CH2:8][N:9]2[S:13][C:12]3[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=3[S:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC1C=C(C=CC=1)C(OO)=[O:23]>C(Cl)(Cl)Cl>[C:1]1([CH2:7][CH2:8][N:9]2[S:10](=[O:23])[C:11]3[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=3[S:13]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 2-(2-phenylethyl)-1,3,2-benzodithiazole (0.538 g, 2.08 mmol), from Step 2, in 30 mL of chloroform at -20° C., was added portionwise 56% meta-chloroperoxybenzoic acid (mCPBA) (0.64 g, 2 mmol). The reaction mixture was allowed to warm to 0° C. over a 2 hour period and then the reaction was quenched at 10° C. with 20 mL of 1M aqueous sodium bicarbonate solution. The organic layer was concentrated in vacuo and the residue was purified by column chromatography on silica gel eluting with chloroform (CHCl3) to give 389 mg (65.7% yield) of the title compound. Analysis calculated for C14H13NOS2 : C, 61.08; H, 4.76; N, 5.09. Found: C, 60.92; H, 4.75; N, 5.04.

Workup

customthe reaction was quenched at 10° C. with 20 mL of 1M aqueous sodium bicarbonate solution
concentrationThe organic layer was concentrated in vacuo
customthe residue was purified by column chromatography on silica gel eluting with chloroform (CHCl3)

Sources & evidence

ORD record: ord-9f256fac248842bcb15ca02d9f54862b
Source dataset: uspto-grants-1992_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05140018

Reaction notes

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