Water → N-(2-(3,3-dimethylbut-1-ynyl)-5-fluoro-4-nitrophenyl)butyramide

HRID 1964267Notes

Reaction equation

HRID 1964267 reaction equation
[CH3:1][C:2]([CH3:17])([CH3:16])[C:3]#[C:4][C:5]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[C:9]([F:15])=[CH:8][C:6]=1[NH2:7].CCN(CC)CC.[C:25](Cl)(=[O:29])[CH2:26][CH2:27][CH3:28].O>ClCCl>[CH3:1][C:2]([CH3:17])([CH3:16])[C:3]#[C:4][C:5]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[C:9]([F:15])=[CH:8][C:6]=1[NH:7][C:25](=[O:29])[CH2:26][CH2:27][CH3:28]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 8855Butyryl chlorideHCID 591291952-(3,3-Dimethylbut-1-ynyl)-5-fluoro-4-nitroaniline

Product 1

HCID 59129414N-(2-(3,3-dimethylbut-1-ynyl)-5-fluoro-4-nitrophenyl)butyramideYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(3,3-dimethylbut-1-ynyl)-5-fluoro-4-nitroaniline (4.2 g, 17.8 mmol) in dichloromethane (50 mL) and Et3N (10.3 mL, 71.2 mmol) was added butyryl chloride (1.9 g, 17.8 mmol) at 0° C. The mixture was stirred at room temperature for 1 h and then poured into water. The aqueous phase was separated and the organic layer was washed with water (50 mL×2) and brine (100 mL), dried over Na2SO4 and concentrated under reduced pressure to dryness. The residue was washed with ether to give N-(2-(3,3-dimethylbut-1-ynyl)-5-fluoro-4-nitrophenyl)butyramide (3.5 g, 67%), which was used in the next step without further purification.

Workup

  1. customThe aqueous phase was separated
  2. washthe organic layer was washed with water (50 mL×2) and brine (100 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure to dryness
  5. washThe residue was washed with ether

Sources & evidence

ORD record
ord-4cc6028dda0341688623d1f31ff2a323
Source dataset
uspto-grants-2013_04
Patent number
US08415387B2

Reaction notes

Loading…