m-Chloroperbenzoic acid → N-Ethyl-N'-[7-(phenylsulfinyl)-1,3-benzothiazol-2-yl]urea

HRID 9161Notes

Reaction equation

[CH2:1]([NH:3][C:4]([NH:6][C:7]1[S:8][C:9]2[C:15]([S:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:14][CH:13]=[CH:12][C:10]=2[N:11]=1)=[O:5])[CH3:2].C1C=C(Cl)C=C(C(OO)=[O:31])C=1>C(Cl)Cl>[CH2:1]([NH:3][C:4]([NH:6][C:7]1[S:8][C:9]2[C:15]([S:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[O:31])=[CH:14][CH:13]=[CH:12][C:10]=2[N:11]=1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 20 °C

Procedure

To a suspension of N-ethyl-N′-[7-(phenylsulfanyl)-1,3-benzothiazol-2-yl]urea (107 mg, 0.32 mmol) in CH2Cl2 (5 mL) was added MCPBA (60 mg, 0.24 mmol, 70%). The reaction mixture was stirred at about 20° C. for about 1.5 hrs. The reaction mixture was then concentrated in vacuo. The crude reaction mixture was purified by flash chromatography on SiO2 (EtOAc/CH2Cl2 10/90). 32 mg (29%) of pure product was isolated. LC/MS 346 (MH+); RP-HPLC RT 12.96 min.

Workup

concentrationThe reaction mixture was then concentrated in vacuo
customThe crude reaction mixture
customwas purified by flash chromatography on SiO2 (EtOAc/CH2Cl2 10/90)

Sources & evidence

ORD record: ord-ac6888f33d2349549c68bc6416e95d15
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07091227B2

Reaction notes

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