Triethylamine → ethyl N-(1-methylcyclohexylcarbonyl)-2-chloro-6-fluorobenzimidate

HRID 128960Notes

Reaction equation

HRID 128960 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[C:3]=1[C:4](=[NH:8])[O:5][CH2:6][CH3:7].C(N(CC)CC)C.[CH3:21][C:22]1([C:28](Cl)=[O:29])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1>C1(C)C=CC=CC=1>[CH3:21][C:22]1([C:28]([N:8]=[C:4]([O:5][CH2:6][CH3:7])[C:3]2[C:9]([F:13])=[CH:10][CH:11]=[CH:12][C:2]=2[Cl:1])=[O:29])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 41892451-Methylcyclohexanecarbonyl chlorideHCID 18347929Ethyl 2-chloro-6-fluorobenzimidate

Product 1

HCID 19373100ethyl N-(1-methylcyclohexylcarbonyl)-2-chloro-6-fluorobenzimidate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Ethyl 2-chloro-6-fluoro-benzimidate (1.61 g) and triethylamine (1.0 g) are dissolved in toluene (100 ml), to which is added dropwise 1-methylcyclohexylcarbonyl chloride (1.5 g) at 5°-10° C. with stirring and thereafter stirred at room temperature for 1 hour. Further, it is reacted at 80°-100° C. for 16 hours. After the completion of the reaction, the reaction solution is washed with a saline solution and further with water and then the resulting toluene layer is dried on sodium sulfate and concentrated to obtain crude product of ethyl N-(1-methylcyclohexylcarbonyl)-2-chloro-6-fluorobenzimidate.

Workup

  1. stirringstirred at room temperature for 1 hour
  2. customFurther, it is reacted at 80°-100° C. for 16 hours
  3. customAfter the completion of the reaction
  4. washthe reaction solution is washed with a saline solution and further with water
  5. dry with materialthe resulting toluene layer is dried on sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-78beb3a0c5db426f96259fdebd22d18d
Source dataset
uspto-grants-1995_11
Patent number
US05466705

Reaction notes

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