Hydrochloric Acid → HCID 67420541, compound

HRID 2219333Notes

Reaction equation

HRID 2219333 reaction equation
[OH:1]/[N:2]=[C:3](\Cl)/[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[F:10].[C:12]([CH2:15][C:16](=O)[CH3:17])(=[O:14])[CH3:13].[O-]CC.[Na+].Cl>C(O)C>[F:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[C:3]1[C:15]([C:12](=[O:14])[CH3:13])=[C:16]([CH3:17])[O:1][N:2]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 31261AcetylacetoneHCID 2723922Sodium ethoxideHCID 96345772-Fluoro-N-hydroxybenzimidoyl chloride

Product 1

HCID 67420541HCID 67420541, compoundYield 86.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of (E)- and/or (Z)-N-hydroxy-2-fluoro-benzenecarboximidoyl chloride (6.5 g, 37 mmol) in ethanol (29 mL) was added dropwise to a solution of acetylacetone (4.6 g, 46 mmol) containing sodium ethoxide (14.8 g, 46 mmol) in ethanol (83 mL) at ice-bath cooling temperature. After complete addition, the resulting mixture was allowed to warm up to room temperature and stirred for 1.5 h. The mixture was then acidified with HCl (6 N) and concentrated and the mixture extracted with ethyl acetate and then washed with water and brine and dried over sodium sulphate. Purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 75:25) afforded the title compound (7.0 g, 85%) which was obtained as a light yellow liquid. MS: m/e=220.1 [M+H]+.

Workup

  1. temperaturecooling temperature
  2. additionAfter complete addition
  3. concentrationconcentrated
  4. extractionthe mixture extracted with ethyl acetate
  5. washwashed with water and brine
  6. dry with materialdried over sodium sulphate
  7. customPurification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 75:25)

Sources & evidence

ORD record
ord-bb7ba2ac76d54b4d95344f447f574877
Source dataset
uspto-grants-2008_08
Patent number
US07414061B2

Reaction notes

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