m-Chloroperbenzoic acid → 2-[2-(6,7-Dimethoxy-1-isoquinolinyl)phenylsulphinyl]-1H-benzimidazole

HRID 1199468Notes

Reaction equation

HRID 1199468 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[C:9]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[S:21][C:22]1[NH:26][C:25]3[CH:27]=[CH:28][CH:29]=[CH:30][C:24]=3[N:23]=1)=[N:8][CH:7]=[CH:6]2.ClC1C=CC=C(C(OO)=[O:39])C=1>C(Cl)Cl.C(Cl)(Cl)Cl.C([O-])(O)=O.[Na+]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[C:9]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[S:21]([C:22]1[NH:23][C:24]3[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=3[N:26]=1)=[O:39])=[N:8][CH:7]=[CH:6]2

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 198666312-[2-(6,7-Dimethoxy-1-isoquinolinyl)phenylthio]-1H-benzimidazole

Product 1

HCID 150595402-[2-(6,7-Dimethoxy-1-isoquinolinyl)phenylsulphinyl]-1H-benzimidazole

Reagents, catalysts & solvents 2

HCID 516892Sodium BicarbonateSolventHCID 18399249Chloroform dichloromethaneSolvent

Procedure

The product of step (f) above was dissolved in 1:1 CH2Cl2 -CHCl3 (10 ml), treated with 85%m-Chloroperbenzoic acid (24 mg) at -5°, and worked up in aqueous NaHCO3 to give the title compound. NMR (CDCl3)d, 8.5 (d,1H), 8.35 (dd,1H), 7.26 (1H,s), 7.21 (1H,s), 7.7-7.2 (complex,8H), 4.30 (s,3H), 3.85 (s,3H)ppm, mp 250° (d).

Sources & evidence

ORD record
ord-6a337853a57b44b2948d9c56aa4860ed
Source dataset
uspto-grants-1990_02
Patent number
US04900751

Reaction notes

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