Water → HCID 66671906, compound

HRID 1158151Notes

Reaction equation

HRID 1158151 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](CCN)=[C:4]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:3]=1.[CH2:15]([N:17](CC)[CH2:18][CH3:19])[CH3:16].C(Cl)(=[O:24])C.O>ClCCl.CN(C)C1C=CN=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:17]([CH2:18][CH3:19])[C:15](=[O:24])[CH3:16])=[C:4]([C:11]([CH3:12])([CH3:13])[CH3:14])[CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 66671971HCID 66671971, compound

Product 1

HCID 66671906HCID 66671906, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

In a 250 mL three-necked flask under a nitrogen atmosphere, equipped with a magnetic stirrer, 15 g (58.5 mmol) of (4-bromo-2-tert-butylphenyl)ethylamine are dissolved in 150 mL of dichloromethane. 8.9 g (87.8 mmol, 12.2 mL) of triethylamine and 0.72 g (5.9 mmol) of 4-dimethylaminopyridine are added. 11.5 g (146 mmol, 2.5 mL) of acetyl chloride are added dropwise and the reaction medium is stirred for 1 hour at room temperature. The reaction medium is poured into 250 mL of water and extracted twice with dichloromethane. The organic phases obtained are combined and washed with water, dried over anhydrous magnesium sulfate, filtered and evaporated to give a blackish oil. This oil is purified by chromatography on silica (eluent: 80/20 heptane/ethyl acetate) to give 15 g (yield=86%) of N-(4-bromo-2-tert-butylphenyl)-N-ethylacetamide in the form of an orange oil.

Workup

  1. customIn a 250 mL three-necked flask under a nitrogen atmosphere, equipped with a magnetic stirrer
  2. extractionextracted twice with dichloromethane
  3. customThe organic phases obtained
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customto give a blackish oil
  9. customThis oil is purified by chromatography on silica (eluent: 80/20 heptane/ethyl acetate)

Sources & evidence

ORD record
ord-7cce7c75585a4dbf872f002d9ee1e7c2
Source dataset
uspto-grants-2010_10
Patent number
US07807708B2

Reaction notes

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