Benzyl Bromide → HCID 20523224, compound

HRID 223149Notes

Reaction equation

HRID 223149 reaction equation
[CH2:1]([Br:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:9][N:10]=[CH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1>CN(C)C=O>[Br-:8].[CH2:1]([N+:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[CH2:11][NH:10][OH:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 13395Pyridine 2-aldoxime

Product 1

HCID 20523224HCID 20523224, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 25.7 grams (115 mmoles) benzyl bromide and 16.7 grams (137 mmoles) 2-hydroxyiminomethyl-pyridine in dimethyl formamide (70 ml) was stored 7 days at room temperature. The precipitate was filtered off and washed with ethanol and ether. Recrystallization from 96% ethanol yielded 30.9 gram (77%) of the compound 1 in the form of white crystals. (a) In case (hetero)arylmethyl chlorides were used instead of bromides or iodides the reaction mixture was heated at 60°-90° C. for 3 to 4 hours. (b) Cyclohexylmethyl iodide alkylated 2-hydroxyiminomethylpyridine with great difficulty. After reaction at 100° C. for 10 hours a product was precipitated with ether. Recrystallisation yielded a mixture of compound 30 and of the hydroiodide of 2-hydroxyiminomethyl-pyridine from which the compound 30 could be recovered by washing with water.

Workup

  1. filtrationThe precipitate was filtered off
  2. washwashed with ethanol and ether
  3. customRecrystallization from 96% ethanol

Sources & evidence

ORD record
ord-c7d399aac7f14fe89b62a41a44219144
Source dataset
uspto-grants-1982_10
Patent number
US04352810

Reaction notes

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