Trifluoroacetic acid → HCID 22921543, compound

HRID 2258609Notes

Reaction equation

HRID 2258609 reaction equation
CC(C)CNC1C=C(NC(OCC)=[O:14])C=CC=1N.[F:19][C:20]([F:25])([F:24])[C:21]([OH:23])=O.[CH3:26][CH:27]([CH3:48])[CH2:28][N:29]1[C:33]2[CH:34]=[C:35]([NH:38][C:39]([O:41][CH2:42][CH3:43])=[O:40])[CH:36]=[CH:37][C:32]=2[N:31]=[C:30]1[C:44]([F:47])([F:46])[F:45]>C1(C)C=CC=CC=1>[F:45][C:44]([F:47])([F:46])[C:30]([NH:31][C:32]1[CH:37]=[CH:36][C:35]([NH:38][C:39]([O:41][CH2:42][CH3:43])=[O:40])=[CH:34][C:33]=1[N:29]([C:21]([C:20]([F:25])([F:24])[F:19])=[O:23])[CH2:28][CH:27]([CH3:48])[CH3:26])=[O:14]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 22921557HCID 22921557, compoundHCID 22921585HCID 22921585, compound

Product 1

HCID 22921543HCID 22921543, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In yet another example, when 2-(2-methylpropylamino)-4-(ethoxycarbonylamino)aniline (R is 2-methylpropyl, X is hydrogen) (13) was treated with trifluoroacetic acid in toluene as described above (Step D of Example 7), a 1:1 mixture of the intermediate 1-(2-methylpropyl)-2-trifluoromethyl-6-ethoxycarbonylaminobenzimidazole (6), and the uncyclized intermediate, N-trifluoromethylcarbonyl-2-[(trifluoromethylcarbonyl)(2-methylpropyl)amino]-4-(ethoxycarbonylamino)aniline (14) was obtained. Treatment of the mixture of the intermediate benzimidazole (6) and (14) with potassium carbonate and water in methanol resulted in the direct conversion of intermediate (14) to the intermediate benzimidazole (6).

Sources & evidence

ORD record
ord-90f5da147ffd4929a35ba84d64bb3447
Source dataset
uspto-grants-1997_08
Patent number
US05661108

Reaction notes

Loading…