1,3-Dichloroacetone → HCID 22478818, compound

HRID 2182464Notes

Reaction equation

HRID 2182464 reaction equation
[C:1]([CH2:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1)(=[S:3])[NH2:2].[Cl:14][CH2:15][C:16]([CH2:18]Cl)=O>C1COCC1>[Cl:14][CH2:15][C:16]1[N:2]=[C:1]([CH2:4][C:5]2[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=2)[S:3][CH:18]=1

Participants

4

Reactant 2

HCID 107931,3-DichloroacetoneHCID 22478982HCID 22478982, compound

Product 1

HCID 22478818HCID 22478818, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 250 (729 mg, 3.73 mmol) and 1,3-dichloroacetone (474 mg, 3.73 mmol) in THF (30 ml) was stirred at 40° C. during 48h. The solvent was evaporated then the residue was dissolved in ethyl acetate, washed with brine, dried over anhydrous MgSO4, filtered and concentrated. The crude residue was purified by flash chromatography on silica gel (2-4% MeOH/CH2Cl2) to afford the title compound (827 mg, 83% yield) as a white solid. 1H NMR (DMSO) δ (ppm): 12.93 (bs, 1H), 7.91 (d, J=8.1 Hz, 2H), 7.63 (s, 1H), 7.46 (d, J=8.1 Hz, 2H), 4.78 (s, 2H), 4.42 (s, 2H).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude residue was purified by flash chromatography on silica gel (2-4% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-f92121ff8f234c5cbe86d28fbf62ae45
Source dataset
uspto-grants-2005_05
Patent number
US06897220B2

Reaction notes

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