Water → HCID 86635727, compound

HRID 1013347Notes

Reaction equation

HRID 1013347 reaction equation
[Cl:1]N1C(=O)CCC1=O.[C:9]([C:13]1[CH:21]=[CH:20][C:16]([CH:17]=[N:18][OH:19])=[CH:15][CH:14]=1)([CH3:12])([CH3:11])[CH3:10].O>CN(C=O)C>[Cl:1][C:16]1([CH:17]=[N:18][OH:19])[CH:15]=[CH:14][C:13]([C:9]([CH3:12])([CH3:10])[CH3:11])=[CH:21][CH2:20]1

Participants

5

Reactant 3

HCID 962WaterHCID 31398ChlorosuccinimideHCID 1275951N-[(4-tert-butylphenyl)methylidene]hydroxylamine

Product 1

HCID 86635727HCID 86635727, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-chlorosuccinimide (8.1 g, 61 mmol) was added to a solution of 4-tert-butylbenzaldehyde oxime (9 g, 50.1 mmol) in DMF (50 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-hydroxyiminomethyl-4-tert-butylbenzene was obtained as a yellowish solid (10.7 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-51f3bd5e1fb649ab93c0969207e4b95d
Source dataset
uspto-grants-2011_07
Patent number
US07981883B2

Reaction notes

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