Hydrochloric Acid → N-(4-n-pentyloxybenzoyl)-N,O-dimethylhydroxylamine

HRID 351537Notes

Reaction equation

HRID 351537 reaction equation
[CH2:1]([O:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH3:5].C(Cl)(=O)C(Cl)=O.[CH3:22][NH:23][O:24][CH3:25].Cl.C(OC1C=CC(C(Cl)=O)=CC=1)CCCC>C1(C)C=CC=CC=1.O1CCCC1.N1C=CC=CC=1.CN(C)C=O>[CH2:1]([O:6][C:7]1[CH:8]=[CH:9][C:10]([C:11]([N:23]([CH3:22])[O:24][CH3:25])=[O:13])=[CH:14][CH:15]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

10

Reactant 5

HCID 313Hydrochloric Acid2×HCID 14232N,O-DimethylhydroxylamineHCID 65578Oxalyl chlorideHCID 85153Benzoic acid, 4-(pentyloxy)-HCID 94910p-Pentoxybenzoyl chloride

Product 1

HCID 22713252N-(4-n-pentyloxybenzoyl)-N,O-dimethylhydroxylamine

Reagents, catalysts & solvents 4

HCID 1049PyridineSolventHCID 1140TolueneSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 4-n-pentyloxybenzoic acid (5.0 g) in toluene was added oxalyl chloride (15 ml) and N,N-dimethylformamide (0.1 ml) and the mixture was stirred for 2 hours at room temperature. The solvents were evaporated under reduced pressure to give crude 4-n-pentyloxybenzoyl chloride. To a suspension of N,O-dimethylhydroxylamine a hydrochloride (3.51 g) and pyridine (5.82 ml) in tetrahydrofuran (25 ml) was added the solution of crude 4-n-pentyloxybenzoyl chloride in tetrahydrofuran (25 ml) dropwise at 0° C. and the mixture was stirred for 3 hours at room temperature. To the reaction mixture 1N HCl was added and extracted with ethyl acetate. The organic layer was separated, washed with water and brine, dried over magnesium sulfate and evaporated under reduced pressure to give N-(4-n-pentyloxybenzoyl)-N,O-dimethylhydroxylamine (4.63 g).

Workup

  1. customThe solvents were evaporated under reduced pressure
  2. customto give crude 4-n-pentyloxybenzoyl chloride
  3. stirringthe mixture was stirred for 3 hours at room temperature
  4. extractionextracted with ethyl acetate
  5. customThe organic layer was separated
  6. washwashed with water and brine
  7. dry with materialdried over magnesium sulfate
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-12a0b63b4cde4eee8a712bc2e9c58201
Source dataset
uspto-grants-2004_06
Patent number
US06743776B2

Reaction notes

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