4-Fluorobenzoic Acid → HCID 14097619, compound

HRID 1762180Notes

Reaction equation

HRID 1762180 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][CH:6]=1.[F:15][C:16]1[CH:24]=[CH:23][C:19]([C:20](O)=[O:21])=[CH:18][CH:17]=1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O>[F:15][C:16]1[CH:24]=[CH:23][C:19]([C:20]([NH:1][CH2:2][CH2:3][O:4][C:5]2[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][CH:6]=2)=[O:21])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 99734-Fluorobenzoic AcidHCID 10868DicyclohexylcarbodiimideHCID 14097616Methyl 4-(2-aminoethoxy)benzoate

Product 1

HCID 14097619HCID 14097619, compoundYield 67.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl 4-(2-aminoethoxy)benzoate (19.5 g) and 14 g of p-fluorobenzoic acid were dissolved in 300 ml of N,N-dimethylformamide and 20.6 g of N,N'-dicyclohexylcarbodiimide was added thereto little by little with stirring at room temperature. The mixture was stirred for 8 hours, the resulting N,N'-dicyclohexylurea was removed by filtration, the filtrate was poured into ice water, and the mixture was extracted with ethyl acetate. The organic layer was washed with 10% hydrochloric acid, saturated potassium carbonate solution, and water. This was dried with anhydrous magnesium sulphate, concentrated in vacuo, the residue was crystallised with n-hexane, and the resulting 25.4 g of crystals were recrystallised from ethyl acetate/n-hexane to give 21.3 g (yield: 67%) of crystalline product. M.p. 105°-107° C.

Workup

  1. stirringThe mixture was stirred for 8 hours
  2. customthe resulting N,N'-dicyclohexylurea was removed by filtration
  3. additionthe filtrate was poured into ice water
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with 10% hydrochloric acid, saturated potassium carbonate solution, and water
  6. dry with materialThis was dried with anhydrous magnesium sulphate
  7. concentrationconcentrated in vacuo
  8. customthe residue was crystallised with n-hexane
  9. customthe resulting 25.4 g of crystals were recrystallised from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-c4131f41f59f47a6bb7b166686cd5ba7
Source dataset
uspto-grants-1989_05
Patent number
US04831055

Reaction notes

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