Water → n-Hydroxy-4-(4-isopropoxyphenoxy)benzenecarboximidoyl chloride

HRID 404881Notes

Reaction equation

HRID 404881 reaction equation
[CH:1]([O:4][C:5]1[CH:20]=[CH:19][C:8]([O:9][C:10]2[CH:18]=[CH:17][C:13]([CH:14]=[N:15][OH:16])=[CH:12][CH:11]=2)=[CH:7][CH:6]=1)([CH3:3])[CH3:2].[Cl:21]N1C(=O)CCC1=O.O>CN(C)C=O>[OH:16][N:15]=[C:14]([Cl:21])[C:13]1[CH:17]=[CH:18][C:10]([O:9][C:8]2[CH:19]=[CH:20][C:5]([O:4][CH:1]([CH3:3])[CH3:2])=[CH:6][CH:7]=2)=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 31398ChlorosuccinimideHCID 1317316044-(4-Isopropoxyphenoxy)benzaldehyde oxime

Product 1

HCID 131731605n-Hydroxy-4-(4-isopropoxyphenoxy)benzenecarboximidoyl chlorideYield 104.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of Example 17C (1.48 g, 5.56 mmol) in N,N-dimethyl formamide (15 mL) was added N-chlorosuccinimide (0.70 g, 5.24 mmol) at room temperature. The mixture was stirred at room temperature overnight. The mixture was poured into water. The aqueous layer was extracted with ether washed with water, then brine, and dried over MgSO4 and concentrated to give the title compound as an oil (1.67 g, 100%),

Workup

  1. extractionThe aqueous layer was extracted with ether
  2. washwashed with water
  3. dry with materialbrine, and dried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4445b2fac22d455bbc5e5c64ace595d9
Source dataset
uspto-grants-2014_06
Patent number
US08748627B2

Reaction notes

Loading…