Chlorosuccinimide → HCID 86704400, compound

HRID 1748160Notes

Reaction equation

HRID 1748160 reaction equation
[C:1]1([C@@H:7]2[CH2:9][C@H:8]2[CH:10]=[N:11][OH:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:13]N1C(=O)CCC1=O>CN(C=O)C>[OH:12][N:11]=[C:10]([Cl:13])[C@@H:8]1[CH2:9][C@H:7]1[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 86704399HCID 86704399, compound

Product 1

HCID 86704400HCID 86704400, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the crude trans-2-phenylcyclopropanecarbaldehyde oxime rac-I-6C (04 g, 2.51 mmol) in DMF (5 mL) and cooled at 0°C. N-chlorosuccinimide (0.37 g, 2.7 mmol) was added portionwise. The reaction mixture was slowly warmed to rt and stirred fo(14 h. The reaction was quenched with saturated NaCl (aq.) and extracted with Et2O. The organics were collected, washed with water, brine, dried over Na2SO4, filtered, and concentrated under vacuum. The crude was purified by column chromatography on silica gel with hexane-EtOAc (5 to 20% gradient as eluant) to yield trans-N-hydroxy-2-phenylcyclopropanecarbimidoyl chloride.

Workup

  1. custom14 h
  2. customThe reaction was quenched with saturated NaCl (aq.)
  3. extractionextracted with Et2O
  4. customThe organics were collected
  5. washwashed with water, brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customThe crude was purified by column chromatography on silica gel with hexane-EtOAc (5 to 20% gradient as eluant)

Sources & evidence

ORD record
ord-7df2f811d20044dc949fbb4c8878c76b
Source dataset
uspto-grants-2015_10
Patent number
US09150568B2

Reaction notes

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