Isopropanol → HCID 15477194, compound

HRID 840356Notes

Reaction equation

HRID 840356 reaction equation
[CH3:1][CH:2]([OH:4])[CH3:3].C(N(CC)CC)C.[Cl:12][CH:13]([CH2:17][C:18]1[CH:23]=[C:22]([N:24]2[C:28](=[O:29])[C:27]3=[CH:30][CH:31]=[CH:32][CH:33]=[C:26]3[C:25]2=[O:34])[C:21]([F:35])=[CH:20][C:19]=1[Cl:36])[C:14](Cl)=[O:15]>ClCCl>[Cl:12][CH:13]([CH2:17][C:18]1[CH:23]=[C:22]([N:24]2[C:28](=[O:29])[C:27]3=[CH:30][CH:31]=[CH:32][CH:33]=[C:26]3[C:25]2=[O:34])[C:21]([F:35])=[CH:20][C:19]=1[Cl:36])[C:14]([O:4][CH:2]([CH3:3])[CH3:1])=[O:15]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 8471TriethylamineHCID 22623295HCID 22623295, compound

Product 1

HCID 15477194HCID 15477194, compoundYield 68.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In 10 ml of dichloromethane were dissolved 0.18 g of 2-propanol and 0.25 g of triethylamine, and a solution of 1.00 g of 2-chloro-3-(2-chloro-4-fluoro-5-phthalimidophenyl)propionyl chloride prepared by the process described in Example 4 in 15 ml of dichloromethane was slowly added thereto dropwise under stirring. After the dropwise addition, the stirring was continued at room temperature for 1 hour. The reaction mixture was washed successively with water and a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate-hexane=1:8) to give 0.73 g of the title compound (No. 7 of Table 1).

Workup

  1. additionwas slowly added
  2. additionAfter the dropwise addition
  3. washThe reaction mixture was washed successively with water
  4. dry with materiala saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (ethyl acetate-hexane=1:8)

Sources & evidence

ORD record
ord-dc33adf6018d464e903752c646d448e4
Source dataset
uspto-grants-2002_04
Patent number
US06365753B1

Reaction notes

Loading…