Water → 4-benzyloxy-N-hydroxy-2-iodo-5-methoxy-benzimidoylchloride

HRID 2075945Notes

Reaction equation

HRID 2075945 reaction equation
[CH2:1]([O:8][C:9]1[C:17]([O:18][CH3:19])=[CH:16][C:12]([CH:13]=[N:14][OH:15])=[C:11]([I:20])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C)C=O.[Cl:26]N1C(=O)CCC1=O.O>C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[C:17]([O:18][CH3:19])=[CH:16][C:12]([C:13]([Cl:26])=[N:14][OH:15])=[C:11]([I:20])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 31398ChlorosuccinimideHCID 72327488HCID 72327488, compound

Product 1

HCID 866472264-benzyloxy-N-hydroxy-2-iodo-5-methoxy-benzimidoylchloride

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 4-benzyloxy-2-iodo-5-methoxy-benzaldehyde oxime (reference example 2-1) (12.8 g) and N,N-dimethylformamide (110 mL) was added N-chlorosuccinimide (4.9 g) at room temperature. After stirring at room temperature for 20 minutes, water and ethyl acetate were added to the mixture under ice-bath cooling. The separated organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give 4-benzyloxy-N-hydroxy-2-iodo-5-methoxy-benzimidoylchloride.

Workup

  1. temperaturecooling
  2. dry with materialThe separated organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-227e12ebaa54475d8371c5d5d4ffe8e9
Source dataset
uspto-grants-2011_04
Patent number
US07923462B2

Reaction notes

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