4-tert-Butylbenzoyl chloride → HCID 6480852, compound

HRID 855998Notes

Reaction equation

HRID 855998 reaction equation
[C:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9](Cl)=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:14][C:15]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[CH:17][C:16]=1[OH:24]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([NH:14][C:15]2[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[CH:17][C:16]=2[OH:24])=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 743724-tert-Butylbenzoyl chlorideHCID 36133892-Amino-4-Nitrophenol

Product 1

HCID 6480852HCID 6480852, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

4-Dimethylaminopyridine (2.62 g, 21.4 mmol) was added portionwise with stirring to a solution of 4-tert-butylbenzoyl chloride (3.8 ml, 19.5 mmol) and 2-amino-4-nitrophenol (3.0 g, 19.5 mmol) in 60 ml methylene chloride. The resulting solution was stirred overnight at room temperature. The reaction solution was diluted with 60 ml methylene chloride and washed with 3×50 ml water. The methylene chloride solution was separated, filtered to remove precipitated solid, dried (anhydrous sodium sulfate) and concentrated to dryness under reduced pressure to yield the title compound as a brownish solid (5.01 g, 82% yield).

Workup

  1. washwashed with 3×50 ml water
  2. customThe methylene chloride solution was separated
  3. filtrationfiltered
  4. customto remove
  5. customprecipitated solid
  6. dry with materialdried (anhydrous sodium sulfate)
  7. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-d81bb3a65bb843ba82903186ce827ac6
Source dataset
uspto-grants-2007_08
Patent number
US07262318B2

Reaction notes

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