Triethylamine → HCID 47342541, compound

HRID 2054459Notes

Reaction equation

HRID 2054459 reaction equation
[C:1]1([C:7]2[CH:8]=[CH:9][C:10]([NH2:13])=[N:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[CH3:21][C:22]([CH3:27])([CH3:26])[C:23](Cl)=[O:24]>ClCCl>[CH3:21][C:22]([CH3:27])([CH3:26])[C:23]([NH:13][C:10]1[CH:9]=[CH:8][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:12][N:11]=1)=[O:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 1050975-Phenyl-2-pyridinamine

Product 1

HCID 47342541HCID 47342541, compoundYield 71.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-phenylpyridin-2-amine (2.4 g, 14.10 mmol) was dissolved in 75 ml of dichloromethane. The solution was treated with triethylamine (1.57 g, 15.51 mmol) and trimethylacetylchloride (1.87 g, 15.51 mmol) and the mixture was stirred at room temperature for 1 hour. Silica gel (9 g) was added and the solvent was removed in vacuo. The residue was chromatographed on silica gel eluting with hexanes/ethyl acetate (5:1) to afford 2,2-dimethyl-N-(5-phenylpyridin-2-yl)propanamide (2.58 g) as a white solid.

Workup

  1. additionSilica gel (9 g) was added
  2. customthe solvent was removed in vacuo
  3. customThe residue was chromatographed on silica gel eluting with hexanes/ethyl acetate (5:1)

Sources & evidence

ORD record
ord-b816787968a447edb99deaf640188359
Source dataset
uspto-grants-2008_02
Patent number
US07329678B2

Reaction notes

Loading…