Methanol → 1-Isopropylsulfonyl-2-amino-6-(1-phenyl-1-hydroxy-1-propyl)benzimidazole

HRID 2295359Notes

Reaction equation

HRID 2295359 reaction equation
[C:1](=[C:3]1N=C2C=CC=CC2=N1)=O.[CH:12]([S:15]([N:18]1[C:22]2[CH:23]=[C:24]([C:27](=[O:34])[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH:25]=[CH:26][C:21]=2[N:20]=[C:19]1[NH2:35])(=[O:17])=[O:16])([CH3:14])[CH3:13].C([Mg]Br)C.CO>C(OCC)C>[CH:12]([S:15]([N:18]1[C:22]2[CH:23]=[C:24]([C:27]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)([OH:34])[CH2:1][CH3:3])[CH:25]=[CH:26][C:21]=2[N:20]=[C:19]1[NH2:35])(=[O:16])=[O:17])([CH3:14])[CH3:13]

Participants

6

Reactant 4

HCID 887MethanolHCID 30173892-Amino-6-benzoyl-1-((isopropyl)sulphonyl)-1H-benzimidazoleHCID 22387228Carbonyl benzimidazoleHCID 178418443HCID 178418443, compound

Product 1

HCID 204753751-Isopropylsulfonyl-2-amino-6-(1-phenyl-1-hydroxy-1-propyl)benzimidazole

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The 1-hydroxy-1-(C1 -C7 alkyl)benzyl derivatives, the carbinols, can also be prepared by reacting the corresponding carbonyl derivative with the appropriate Grignard reagent followed by hydrolysis. The carbonyl benzimidazole, 1-isopropylsulfonyl-2-amino-6-benzoylbenzimidazole, is reacted with ethylmagnesium bromide in anhydrous ethyl ether and then hydrolyzed to form the carbinol, 1-isopropylsulfonyl-2-amino-6-(1-phenyl-1-hydroxy-1-propyl)benzimidazole. The Grignard reagent, ethylmagnesium bromide, is made from ethylbromide and metallic magnesium in anhydrous ethyl ether.

Workup

  1. customfollowed by hydrolysis

Sources & evidence

ORD record
ord-a23a89d736354c4ea5c7fe5e88f304f0
Source dataset
uspto-grants-1984_01
Patent number
US04424362

Reaction notes

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