4-Chlorobenzoic Acid → 2-(4-Chlorophenyl)-5-nitrobenzimidazole

HRID 2243088Notes

Reaction equation

HRID 2243088 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=O)=[CH:4][CH:3]=1.[NH2:11][C:12]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][C:13]=1[NH2:14]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]2[NH:14][C:13]3[CH:15]=[C:16]([N+:19]([O-:21])=[O:20])[CH:17]=[CH:18][C:12]=3[N:11]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 63184-Chlorobenzoic AcidHCID 51117914-Nitro-1,2-phenylenediamine

Product 1

HCID 3763532-(4-Chlorophenyl)-5-nitrobenzimidazoleYield 87%

Reagents, catalysts & solvents 1

HCID 21584019Toluene ethylacetateSolvent

Procedure

Prepared from 4-chlorobenzoic acid (17.83 g, 0.114 mol) and 2-amino-5-nitroaniline (18 g, 0.114 mol), in a manner similar to that of Example 9b. Yield: 87%; Rf (6/4 toluene/ethyl acetate): 0.61; m.p.: 302.5-305° C.

Sources & evidence

ORD record
ord-485e980b42c54534940b73b1b748e46c
Source dataset
uspto-grants-2010_03
Patent number
US07674809B2

Reaction notes

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