N-chlorosuccinamide → HCID 86669882, compound

HRID 1506357Notes

Reaction equation

HRID 1506357 reaction equation
[CH2:1]([C:4]1[CH:12]=[CH:11][C:7]([CH:8]=[N:9][OH:10])=[CH:6][CH:5]=1)[CH2:2][CH3:3].[Cl:13]NC(=O)CCC(N)=O>CN(C)C=O>[OH:10][N:9]=[C:8]([Cl:13])[C:7]1[CH:11]=[CH:12][C:4]([CH2:1][CH2:2][CH3:3])=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 15238416N-chlorosuccinamideHCID 86669883HCID 86669883, compound

Product 1

HCID 86669882HCID 86669882, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 4-propylbenzaldehyde oxime (1.4 g, 8.58 mmol) in dimethylformamide (3 mL) was added N-chlorosuccinamide (1.145 g, 8.58 mmol) in batches over a period of 10 min. at room temperature. The reaction mixture was stirred at that temperature for an additional 10 min., and partitioned between ethyl acetate (20 mL) and brine (2×20 mL). The ethyl acetate layer was dried over sodium sulfate and purified by silica gel column chromatography using hexane and ethyl acetate. Fractions corresponding to the desired product were collected and concentrated to yield the title compound, which was immediately used for the subsequent step. LCMS M+1=198.

Workup

  1. custompartitioned between ethyl acetate (20 mL) and brine (2×20 mL)
  2. dry with materialThe ethyl acetate layer was dried over sodium sulfate
  3. custompurified by silica gel column chromatography
  4. customFractions corresponding to the desired product were collected
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-882d3746fc0e42d2891b55737e4db5cd
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

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