Acetone → HCID 86672155, compound

HRID 1842944Notes

Reaction equation

HRID 1842944 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[CH2:9][O:10][CH2:11][CH2:12][O:13][CH3:14])[NH2:5].N1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.ClC(OC1C=CC=CC=1)=[O:23].C[C:32]([CH3:34])=[O:33]>>[C:32]([O:23][NH:5][C:4]1[CH:6]=[CH:7][C:8]([CH2:9][O:10][CH2:11][CH2:12][O:13][CH3:14])=[C:2]([F:1])[CH:3]=1)(=[O:33])[C:34]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 4

HCID 180AcetoneHCID 1049PyridineHCID 15891Phenyl chloroformateHCID 64768098HCID 64768098, compound

Product 1

HCID 86672155HCID 86672155, compound

Procedure

To a stirred solution of 3-fluoro-4-((2-methoxyethoxy)methyl)aniline (2.5 g, 13.0 mmol, 1 eq) in acetone (25 mL) was added pyridine (3.15 mL, 39.0 mmol, 3 eq) followed by phenyl chloroformate (1.64 mL, 13.0 mmol, 1 eq) at 0° C. and the mixture was stirred at RT for 1 h. The solvent was evaporated and resulting residue was purified by CC using ethyl acetate/PE (3:7) as eluent to get O-benzoyl-N-(3-fluoro-4-((2-methoxyethoxy)methyl)phenyl)-hydroxylamine as white solid (TLC system: EtOAc/PE (1:1), Rf: 0.4).

Workup

  1. customThe solvent was evaporated
  2. customresulting residue
  3. customwas purified by CC

Sources & evidence

ORD record
ord-de7aa2e7744b4ac9a125ab60a4dbf4b5
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

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