p-Toluenesulfonic acid → 1-(1-(3-bromophenyl)-1H-benzo[d]imidazol-5-yl)ethanone

HRID 2262742Notes

Reaction equation

HRID 2262742 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:16](=[O:18])[CH3:17])[CH:5]=[CH:6][C:7]=1[NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([Br:15])[CH:10]=1.[CH:19](OCC)(OCC)OCC.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1COCC1>[Br:15][C:11]1[CH:10]=[C:9]([N:8]2[C:7]3[CH:6]=[CH:5][C:4]([C:16](=[O:18])[CH3:17])=[CH:3][C:2]=3[N:1]=[CH:19]2)[CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 31214Ethyl orthoformateHCID 539889461-[3-Amino-4-(3-bromo-phenylamino)-phenyl]-ethanone

Product 1

HCID 540303071-(1-(3-bromophenyl)-1H-benzo[d]imidazol-5-yl)ethanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

This was prepared from 1-[3-amino-4-(3-bromo-phenylamino)-phenyl]-ethanone (86.5 g, 0.28 mol) by treatment with triethyl orthoformate in THF in the presence of p-toluenesulfonic acid as described in Example 1.

Sources & evidence

ORD record
ord-a1b5c198050f45bb8d5cbcb3a7a1ed36
Source dataset
uspto-grants-2010_12
Patent number
US07851490B2

Reaction notes

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