Benzaldehyde → 7-Benzylidenamino-1-ethyl-2-methyl-5-trifluoromethyl-6-chlorobenzimidazole

HRID 46720

Reaction equation

HRID 46720 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:9]([N:11]1[C:15]2[C:16]([NH2:25])=[C:17]([Cl:24])[C:18]([C:20]([F:23])([F:22])[F:21])=[CH:19][C:14]=2[N:13]=[C:12]1[CH3:26])[CH3:10].C1(S(O)(=O)=O)C=CC=CC=1>C1(C)C(C)=CC=CC=1>[CH:1](=[N:25][C:16]1[C:15]2[N:11]([CH2:9][CH3:10])[C:12]([CH3:26])=[N:13][C:14]=2[CH:19]=[C:18]([C:20]([F:22])([F:23])[F:21])[C:17]=1[Cl:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 7371Benzenesulfonic AcidHCID 142814196-Chloro-1-ethyl-2-methyl-5-(trifluoromethyl)-1H-benzimidazol-7-amine

Product 1

HCID 203853817-Benzylidenamino-1-ethyl-2-methyl-5-trifluoromethyl-6-chlorobenzimidazoleYield 94%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

Benzaldehyde (0.78 g.; 7.35 mmole) was reacted with 1-ethyl-2-methyl-5-trifluoromethyl-6-chloro-7-aminobenzimidazole (1.0 g.; 3.66 mmole) in the presence of 7 ml. of xylene and a few crystals of benzenesulfonic acid. The mixture was refluxed for 1 hour, removing water from the reaction mixture. Upon cooling to room temperature, the product crystallized out of solution to give 1.24 g. (94% yield). After recrystallization from benzene, the product melts at 183°-185.5° C.

Workup

  1. temperatureThe mixture was refluxed for 1 hour
  2. customremoving water from the reaction mixture
  3. customthe product crystallized out of solution
  4. customto give 1.24 g
  5. customAfter recrystallization from benzene

Sources & evidence

ORD record
ord-dee3b648626c42eaa7460360357e10a3
Source dataset
uspto-grants-1979_11
Patent number
US04174959

Linked notes

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