Chloroacetone → HCID 58135242, compound

HRID 1893542Notes

Reaction equation

HRID 1893542 reaction equation
C([O:3][C:4](=[O:23])[CH2:5][N:6]([CH2:17][C:18]([O:20]CC)=[O:19])[C:7]1[CH:12]=[C:11]([C:13]([NH2:15])=[S:14])[CH:10]=[CH:9][C:8]=1[CH3:16])C.Cl[CH2:25][C:26](=O)[CH3:27]>C(O)C.CN(C)C=O>[CH3:16][C:8]1[CH:9]=[CH:10][C:11]([C:13]2[S:14][CH:25]=[C:26]([CH3:27])[N:15]=2)=[CH:12][C:7]=1[N:6]([CH2:5][C:4]([OH:3])=[O:23])[CH2:17][C:18]([OH:20])=[O:19]

Participants

5

Reactant 2

HCID 6571ChloroacetoneHCID 86650781HCID 86650781, compound

Product 1

HCID 58135242HCID 58135242, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

The compound (0.70 g, 2.1 mmol) obtained in step A was dissolved in a ethanol (14 ml)-N,N-dimethylformamide (4 ml) mixed solvent. Then, chloroacetone (0.18 ml, 2.3 mmol) was added, and the mixture was stirred at 80° C. for 3 hr. The reaction mixture was concentrated under reduced pressure, and the obtained oil was diluted with dichloromethane, washed with water, saturated aqueous sodium hydrogen carbonate and saturated brine, and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the solution was concentrated under reduced pressure to give a crude oil of the title compound containing N,N-dimethylformamide. Using this oil and according to the method of Reference Example 62, step B, the title compound (0.56 g, yield 83%) was obtained as a pale-yellow oil.

Workup

  1. additionmixed solvent
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionthe obtained oil was diluted with dichloromethane
  4. washwashed with water, saturated aqueous sodium hydrogen carbonate and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationThe insoluble material was filtered off
  7. concentrationthe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b9ea0110e6c24b8e906d55f58cc81d57
Source dataset
uspto-grants-2013_08
Patent number
US08513235B2

Reaction notes

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