Formamide → p-(tert-Butyl)benzamide

HRID 2306140Notes

Reaction equation

HRID 2306140 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:11])([CH3:10])[CH3:9])=[CH:4][CH:3]=1.[CH:12]([NH2:14])=[O:13]>CN(C)C1C=CN=CC=1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC(N(C)C)=O>[C:8]([C:5]1[CH:6]=[CH:7][C:2]([C:12]([NH2:14])=[O:13])=[CH:3][CH:4]=1)([CH3:11])([CH3:10])[CH3:9]

Participants

6

Reactant 2

HCID 713FormamideHCID 775951-Bromo-4-tert-butylbenzene

Product 1

HCID 92014p-(tert-Butyl)benzamide

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
120 °C

Procedure

0.255 g of bis(triphenylphosphine)-palladium(II) chloride, 7.36 g of 1-bromo-4-tert-butylbenzene, 3.12 g of formamide, 4.64 g of 4-dimethylamino-pyridine and 25 ml of dimethyl acetamide are placed in a 200 ml glass autoclave. The autoclave is closed, flushed with nitrogen three times and then 5 bars carbon monoxide are applied. The reaction mixture is heated to 120° C. and stirred for 18 hours. It is then cooled, and the solution is diluted with diethylether and water, and extracted. The aqueous phase is extracted by shaking 3 times with diethylether, and afterwards the organic phases are collected, dried over magnesium sulphate and concentrated. The oil obtained is chromatographed over silica gel. The yield of title compound is 33% (part of the product remains in the water phase). 1H-NMR: 1.35 (s, CMe3), 6.21 (br, NH2), 7.45 (d, Ph—H), 7.77 (d, Ph—H); 13C-NMR: 31.5 (CMe3), 35.4 (C—Me), 125.9 (2 Ph—CH), 127.6 (2 Ph—CH), 130.9 (Ph—C), 155.1 (Ph—C), 169.9 (CONH2).

Workup

  1. customThe autoclave is closed
  2. customflushed with nitrogen three times
  3. temperatureIt is then cooled
  4. additionthe solution is diluted with diethylether and water
  5. extractionextracted
  6. extractionThe aqueous phase is extracted
  7. stirringby shaking 3 times with diethylether
  8. customafterwards the organic phases are collected
  9. dry with materialdried over magnesium sulphate
  10. concentrationconcentrated
  11. customThe oil obtained
  12. customis chromatographed over silica gel

Sources & evidence

ORD record
ord-298f288b98144ef6ba1f9b9d486a4ae6
Source dataset
uspto-grants-2002_08
Patent number
US06441233B1

Reaction notes

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