HCID 22921571, compound → HCID 22921563, compound

HRID 2258622Notes

Reaction equation

HRID 2258622 reaction equation
[F:1][C:2]([F:29])([F:28])[C:3]([N:5]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=1)[C:6]1[CH:12]=[C:11]([NH:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:10]([F:19])=[CH:9][C:7]=1[NH2:8])=O>C1(C)C=CC=CC=1>[Cl:27][C:23]1[CH:22]=[C:21]([CH2:20][N:5]2[C:6]3[CH:12]=[C:11]([NH:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:10]([F:19])=[CH:9][C:7]=3[N:8]=[C:3]2[C:2]([F:29])([F:28])[F:1])[CH:26]=[CH:25][CH:24]=1

Participants

3

Reactant 1

HCID 22921571HCID 22921571, compound

Product 1

HCID 22921563HCID 22921563, compoundYield 85.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A stirred solution of 3.2 grams (0.007 mole) of 2-[(trifluoromethylcarbonyl)(3-chlorophenylmethyl)amino]-4-ethoxycarbonylamino-5-fluoroaniline in 100 mL of toluene was heated at reflux for about 4.5 hours. After this time, the reaction mixture was concentrated under reduced pressure to a residue, which was triturated with petroleum ether, and the resultant solid was collected by filtration, yielding 2.5 grams of 1-(3-chlorophenylmethyl)-2-trifluoromethyl-5-fluoro-6-ethoxycarbonylaminobenzimidazole, mp 144°-146° C. The NMR spectrum was consistent with the proposed structure.

Workup

  1. temperatureat reflux for about 4.5 hours
  2. concentrationAfter this time, the reaction mixture was concentrated under reduced pressure to a residue, which
  3. customwas triturated with petroleum ether
  4. filtrationthe resultant solid was collected by filtration

Sources & evidence

ORD record
ord-3fb4bd9db1fe43719a78a8b679086b87
Source dataset
uspto-grants-1997_08
Patent number
US05661108

Reaction notes

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