Triethylamine → HCID 66939034, compound

HRID 1591905Notes

Reaction equation

HRID 1591905 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[F:11][C:12]1[CH:13]=[C:14]([NH2:19])[CH:15]=[C:16]([NH2:18])[CH:17]=1.C(N(CC)CC)C>C1COCC1>[NH2:19][C:14]1[CH:15]=[C:16]([NH:18][C:6](=[O:7])[C:5]2[CH:9]=[CH:10][C:2]([F:1])=[CH:3][CH:4]=2)[CH:17]=[C:12]([F:11])[CH:13]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 678794-Fluorobenzoyl chlorideHCID 234235475-Fluorobenzene-1,3-diamine

Product 1

HCID 66939034HCID 66939034, compoundYield 60.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add slowly 4-fluorobenzoyl chloride (403 mg, 2.54 mmol) to a solution of 5-fluoro-benzene-1,3-diamine (Preparation 32 320 mg, 2.54 mmol) in triethylamine (514 mg, 0.71 mL, 5.08 mmol) and THF (10 mL) at 0° C. Stir the mixture overnight and gradually raise to room temperature. Quench the reaction with 0.1N NaOH solution, and extract the mixture with ethylacetate three times. Combine the organic layers and wash with saturated NaCl solution, dry over Na2SO4, filter and concentrate to give a solid. Purify by chromatography (silica gel, eluting with 25–40% ethylacetate in hexanes) gives 379 mg (60%) of N-(3-amino-5-fluoro-phenyl)-4-fluoro-benzamide.

Workup

  1. customQuench
  2. customthe reaction with 0.1N NaOH solution
  3. extractionextract the mixture with ethylacetate three times
  4. washCombine the organic layers and wash with saturated NaCl solution
  5. dry with materialdry over Na2SO4
  6. filtrationfilter
  7. concentrationconcentrate
  8. customto give a solid
  9. customPurify by chromatography (silica gel, eluting with 25–40% ethylacetate in hexanes)

Sources & evidence

ORD record
ord-cff71eeec3de447dbd4cc704fd236a06
Source dataset
uspto-grants-2007_11
Patent number
US07291632B2

Reaction notes

Loading…