Triethylamine → HCID 79035731, compound

HRID 930429Notes

Reaction equation

HRID 930429 reaction equation
[Cl:1][C:2]1[C:10]([F:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].Cl.[CH3:13][NH:14][O:15][CH3:16].C(N(CC)CC)C>CN(C=O)C>[Cl:1][C:2]1[C:10]([F:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([N:14]([O:15][CH3:16])[CH3:13])=[O:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 3026202-Chloro-3-fluorobenzoic acid

Product 1

HCID 79035731HCID 79035731, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-chloro-3-fluorobenzoic acid (3.32 g, 19.02 mmol) in DMF (60 mL) was added N,O-dimethylhydroxylamine hydrochloride, 98% (2.30 g, 23.58 mmol), O-(-7-azabenzotriazol-1-yl)-N,′N,′N,′N′-tetramethyluronium-hexafluorophosphate (HATU) (8.82 g, 23.20 mmol) and triethylamine (6.63 mL, 47.5 mmol). The mixture was stirred at rt for 3 h. The reaction was quenched with saturated Na2CO3 and extracted with EtOAc. The organic solution was washed with water and brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude was purified by flash chromatography on silica gel (80 g, 10-100% EtOAc/hexane in 25 min) to give 2-chloro-3-fluoro-N-methoxy-N-methylbenzamide as colorless oil, which turned to solid on vacuum (3.95 g, 95% yield). MS m/z=218 [M+H]+. Calculated for C9H9ClFNO2: 217.6.

Workup

  1. customThe reaction was quenched with saturated Na2CO3
  2. extractionextracted with EtOAc
  3. washThe organic solution was washed with water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude was purified by flash chromatography on silica gel (80 g, 10-100% EtOAc/hexane in 25 min)

Sources & evidence

ORD record
ord-6999b801936b49349743705942f9cc01
Source dataset
uspto-grants-2016_03
Patent number
US09296734B2

Reaction notes

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