Water → HCID 86624330, compound

HRID 1619730Notes

Reaction equation

HRID 1619730 reaction equation
[Cl:1]N1C(=O)CCC1=O.[CH:9](=[N:16][OH:17])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.O>CN(C=O)C>[Cl:1][C:10]1([CH:9]=[N:16][OH:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH2:11]1

Participants

5

Reactant 3

HCID 962WaterHCID 12143(Z)-Benzaldehyde oximeHCID 31398Chlorosuccinimide

Product 1

HCID 86624330HCID 86624330, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-chlorosuccinimide (4.63 g, 34.7 mmol) was added to a solution of benzaldehyde oxime (3.5 g, 28.9 mmol) in DMF (30 ml) at RT, causing the temperature to rise briefly to 50° C. The reaction mixture was cooled in an ice bath, stirred for 3 h at RT, mixed with water (100 ml) while being cooled with ice and extracted with ether (3×100 ml). The combined organic phases were washed with water (150 ml) and sat. aq. NaCl solution (150 ml), dried and the solvent was removed under vacuum. The desired product 1-chloro-1-hydroxyiminomethylbenzene (C) was obtained as a yellowish solid (4.28 g).

Workup

  1. customto rise briefly to 50° C
  2. temperatureThe reaction mixture was cooled in an ice bath
  3. temperaturewhile being cooled with ice
  4. extractionextracted with ether (3×100 ml)
  5. washThe combined organic phases were washed with water (150 ml) and sat. aq. NaCl solution (150 ml)
  6. customdried
  7. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-a9bf91dfc9c145b2b87466f66404fd4d
Source dataset
uspto-grants-2014_07
Patent number
US08772307B2

Reaction notes

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