Triethylamine → HCID 18786115, compound

HRID 1107860Notes

Reaction equation

HRID 1107860 reaction equation
[Br:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[O:4][CH:5]([CH2:9][CH2:10][CH3:11])[C:6](Cl)=[O:7].[CH3:16][NH:17][O:18][CH3:19].C(N(CC)CC)C>ClCCl>[CH3:16][N:17]([C:6](=[O:7])[CH:5]([O:4][C:3]1[CH:12]=[CH:13][CH:14]=[CH:15][C:2]=1[Br:1])[CH2:9][CH2:10][CH3:11])[O:18][CH3:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 14232N,O-DimethylhydroxylamineHCID 54378591HCID 54378591, compound

Product 1

HCID 18786115HCID 18786115, compoundYield 100.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

5.5 g (18.9 mmol) of 2-(2-bromophenoxy)pentanoic acid chloride, 2.03 g (20.8 mmol) of N-methyl-O-methylhydroxylamine and 190 ml of dichloromethane are placed in a 500 ml round-bottomed flask. The solution is cooled to 0° C. and 5.8 ml (41.6 mmol) of triethylamine are slowly added. The solution is stirred for 1 hour at room temperature and then concentrated under vacuum. 100 ml of a molar hydrochloric acid solution are added to the residue and extraction is carried out with 3×100 ml of ethyl ether. The combined organic phases are dried over magnesium sulphate, filtered and concentrated under vacuum to give 6 g of N-methyl-O-methyl-2-(2-bromophenoxy)pentanohydroxamic acid in the form of a colourless oil; quantitative yield.

Workup

  1. concentrationconcentrated under vacuum
  2. addition100 ml of a molar hydrochloric acid solution are added to the residue and extraction
  3. dry with materialThe combined organic phases are dried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-5f5d385ab68f4bfc91c012cf90af4d8b
Source dataset
uspto-grants-2000_05
Patent number
US06063810

Reaction notes

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