Ammonia tetrahydrofuran → 3-Cyclopropyl-4-fluorobenzamide

HRID 1808214Notes

Reaction equation

HRID 1808214 reaction equation
[CH:1]1([C:4]2[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=2[F:13])[C:7](O)=[O:8])[CH2:3][CH2:2]1.[NH3:14].C1COCC1>C1COCC1>[CH:1]1([C:4]2[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=2[F:13])[C:7]([NH2:14])=[O:8])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 21982362Ammonia tetrahydrofuranHCID 401517963-Cyclopropyl-4-fluorobenzoic acid

Product 1

HCID 401517983-Cyclopropyl-4-fluorobenzamideYield 89.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of compound 3-cyclopropyl-4-fluoro-benzoic acid (Preparation 56, 74 g, 0.41 mol, 1 eq) in THF (800 mL) was added N,N′-carbonyldiimidazole (88 g, 0.53 mol, 1.29 eq) at room temperature. The suspension was stirred at room temperature for 3 h, and turned into a brown solution. Ammonia/THF (1 L) was added to the mixture and the resulting mixture was stirred at room temperature overnight. THF was removed in vacuum and the residue was taken up with water (300 mL). The mixture was filtrated and the solid was washed with water (100 mL) and ether (200 mL). The solid was dissolved in DCM (500 mL), dried over sodium sulfate and concentrated in vacuum to title compound as a white solid (66 g, 0.368 mol, 89.7%).

Workup

  1. stirringthe resulting mixture was stirred at room temperature overnight
  2. customTHF was removed in vacuum
  3. filtrationThe mixture was filtrated
  4. washthe solid was washed with water (100 mL) and ether (200 mL)
  5. dissolutionThe solid was dissolved in DCM (500 mL)
  6. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-88e189ef37b54406a178115db6d3ef78
Source dataset
uspto-grants-2013_01
Patent number
US08357711B2

Reaction notes

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