Chlorosuccinimide → (1E)-N-hydroxy-4-phenylmethoxybenzenecarboximidoyl chloride

HRID 75842

Reaction equation

HRID 75842 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12](/[CH:13]=[N:14]\[OH:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:18]N1C(=O)CCC1=O>>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12](/[C:13](/[Cl:18])=[N:14]\[OH:15])=[CH:16][CH:17]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 31398ChlorosuccinimideHCID 5403280(Z)-4-(benzyloxy)benzaldehyde oxime

Product 1

HCID 10901405(1E)-N-hydroxy-4-phenylmethoxybenzenecarboximidoyl chloride

Procedure

To (Z)-4-(benzyloxy)benzaldehyde oxime (11.3 g) in N,N′-Dimethyl formamide (57 ml), N-Chlorosuccinimide (7.98 g) was added and the reaction mixture was stirred for 3 hours and then solvent was evaporated to dark brown residue. To this residue water was added and extracted with Ethyl acetate. Organic layer was collected and dried over Na2SO4 and concentrated to obtain pale brown solid, which was crystallized from DCM-Petroleum ether to obtain the title compound as white solid. Yield: 7.9 g (60%); 1HNMR (DMSO-d6; 300 MHz): δ 12.17 (s, 1H), 7.73 (d, 2H), 7.33-7.47 (m, 5H), 7.11 (d, 2H) 5.16 (s, 2H).

Workup

  1. customsolvent was evaporated to dark brown residue
  2. additionTo this residue water was added
  3. extractionextracted with Ethyl acetate
  4. customOrganic layer was collected
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customto obtain pale brown solid, which
  8. customwas crystallized from DCM-Petroleum ether

Sources & evidence

ORD record
ord-0ef6adba63234c178b2ce0821706cf56
Source dataset
uspto-grants-2014_09
Patent number
US08835428B2

Linked notes

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