m-Chloroperbenzoic acid → 2-[2-(N-isobutyl-N-methylamino)benzylsulfinyl]imidazo[4,5-b]pyridine

HRID 2107338

Reaction equation

HRID 2107338 reaction equation
[CH2:1]([N:5]([C:7]1[CH:23]=[CH:22][CH:21]=[CH:20][C:8]=1[CH2:9][S:10][C:11]1[NH:12][C:13]2[C:14]([N:19]=1)=[N:15][CH:16]=[CH:17][CH:18]=2)[CH3:6])[CH:2]([CH3:4])[CH3:3].ClC1C=CC=C(C(OO)=[O:32])C=1>C(Cl)(Cl)Cl>[CH2:1]([N:5]([C:7]1[CH:23]=[CH:22][CH:21]=[CH:20][C:8]=1[CH2:9][S:10]([C:11]1[NH:12][C:13]2[C:14]([N:19]=1)=[N:15][CH:16]=[CH:17][CH:18]=2)=[O:32])[CH3:6])[CH:2]([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 148394452-[2-(N-isobutyl-N-methylamino)benzylthio]imidazo[4,5-b]pyridine

Product 1

HCID 148394462-[2-(N-isobutyl-N-methylamino)benzylsulfinyl]imidazo[4,5-b]pyridine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2-Mercaptoimidazo[4,5-b]pyridine and 2-(N-isobutyl-N-methylamino)benzyl chloride hydrochloride were reacted in an aqueous ethanol solution in the presence of sodium hydroxide to obtain 2-[2-(N-isobutyl-N-methylamino)benzylthio]imidazo[4,5-b]pyridine in the same manner as in Example 1-(2). The obtained 2-[2-(N-isobutyl-N-methylamino)benzylthio]imidazo[4,5-b]pyridine was oxidized by m-chloroperbenzoic acid in chloroform in the same manner as in Example 9-(3) to give 2-[2-(N-isobutyl-N-methylamino)benzylsulfinyl]imidazo[4,5-b]pyridine as a pale yellow crystalline product. m.p.: 116°-118° C. (decompn.)

Sources & evidence

ORD record
ord-3895279db0d24f64a20273b46b40ecd0
Source dataset
uspto-grants-1990_06
Patent number
US04933458

Linked notes

Loading…