Hexane → HCID 178469886, compound

HRID 1748608Notes

Reaction equation

HRID 1748608 reaction equation
O[NH:2][C:3](=[NH:14])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][CH:5]=1.[C:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])#[CH:16].CCCCCC>C(O)C>[CH2:20]([O:19][C:17]([C:15]1[N:2]=[C:3]([C:4]2[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][CH:5]=2)[NH:14][CH:16]=1)=[O:18])[CH3:21]

Participants

5

Reactant 3

HCID 8058HexaneHCID 12182Ethyl propiolateHCID 178513301HCID 178513301, compound

Product 1

HCID 178469886HCID 178469886, compoundYield 44.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of N-hydroxy-4-(trifluoromethyl)benzamidine (3.0 g) in ethanol (30 ml) was added ethyl acetylenecarboxylate (1.44 g), and stirred at 80° C. for 26 hours. After the solvent was evaporated, diphenylether (15 ml) was added thereto, and additionally stirred at 180° C. for 5.5 hours. After completion of the reaction, the mixture was allowed to cool to room temperature, and n-hexane was added thereto. The insoluble matter was collected by filtration, washed with n-hexane, and then dried to give 2-[4-(trifluoromethyl)phenyl]-1H-imidazole-4-carboxylic acid ethyl ester (1.84 g).

Workup

  1. customAfter the solvent was evaporated
  2. additiondiphenylether (15 ml) was added
  3. stirringadditionally stirred at 180° C. for 5.5 hours
  4. customAfter completion of the reaction
  5. temperatureto cool to room temperature
  6. filtrationThe insoluble matter was collected by filtration
  7. washwashed with n-hexane
  8. customdried

Sources & evidence

ORD record
ord-86a63614f3b6452bacd5710dde979cd6
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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