Water → HCID 178491142, compound

HRID 2096978Notes

Reaction equation

HRID 2096978 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH2:8])=[CH:5][CH:4]=1.[F:11][C:12]1[C:21]([I:22])=[C:20]([CH3:23])[CH:19]=[CH:18][C:13]=1[C:14](Cl)=[N:15][OH:16].O>O1CCCC1>[F:11][C:12]1[C:21]([I:22])=[C:20]([CH3:23])[CH:19]=[CH:18][C:13]=1[C:14](=[N:15][OH:16])[NH:8][CH2:7][C:6]1[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 754524-MethoxybenzylamineHCID 76688559HCID 76688559, compound

Product 1

HCID 178491142HCID 178491142, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Methoxybenzylamine (2.00 mL, 15.2 mmol) was added dropwise to a solution of 2-fluoro-N-hydroxy-3-iodo-4-methylbenzimidoyl chloride (WO2006094187, 1.46 g, 4.7 mmol) in tetrahydrofuran (20 mL) and the mixture was stirred at ambient temperature overnight. Water was added and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried (MgSO4) and evaporated to give a semi-solid. The solid was triturated with a hexanes/diethyl ether mixture and the solid was filtered and dried to give the title compound (1.66 g, 86%) as a white solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customto give a semi-solid
  6. customThe solid was triturated with a hexanes/diethyl ether mixture
  7. filtrationthe solid was filtered
  8. customdried

Sources & evidence

ORD record
ord-9ae0be327bf64a0cbe86010dbae280f9
Source dataset
uspto-grants-2013_05
Patent number
US08450341B2

Reaction notes

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