Phenylacetyl chloride → N-[4-[2-Ethyl-4-(3-methylphenyl)-1,3-thiazol-5-YL]-2-pyridyl]phenylacetamide

HRID 1268736Notes

Reaction equation

HRID 1268736 reaction equation
[CH2:1]([C:3]1[S:4][C:5]([C:15]2[CH:20]=[CH:19][N:18]=[C:17]([NH2:21])[CH:16]=2)=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[CH:9]=2)[N:7]=1)[CH3:2].[C:22]1([CH2:28][C:29](Cl)=[O:30])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(N(CC)CC)C.C(=O)([O-])O.[Na+]>O1CCCC1>[CH2:1]([C:3]1[S:4][C:5]([C:15]2[CH:20]=[CH:19][N:18]=[C:17]([NH:21][C:29](=[O:30])[CH2:28][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:16]=2)=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[CH:9]=2)[N:7]=1)[CH3:2]

Participants

6

Reactant 4

HCID 7679Phenylacetyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 98573494-[2-ethyl-4-(3-methylphenyl)-1,3-thiazol-5-yl]pyridin-2-amine

Product 1

HCID 10295235N-[4-[2-Ethyl-4-(3-methylphenyl)-1,3-thiazol-5-YL]-2-pyridyl]phenylacetamideYield 67.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-[2-ethyl-4-(3-methylphenyl)-1,3-thiazol-5-yl]-2-pyridylamine (0.80 g, 2.7 mmol) in tetrahydrofuran (8 mL) was added phenylacetyl chloride (0.47 mL, 3.0 mmol), and triethylamine (0.41 mL, 3.0 mmol) was added to the obtained mixture. The reaction mixture was stirred at room temperature for 2 hrs. Saturated aqueous sodium hydrogen carbonate solution was added and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried and concentrated. The residue was purified by silica gel column chromatography (hexane-ethyl acetate 20:1–4:1) and crystallized from isopropyl ether to give the title compound (0.75 g, yield 67%).

Workup

  1. additionwas added to the obtained mixture
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate 20:1–4:1)
  7. customcrystallized from isopropyl ether

Sources & evidence

ORD record
ord-2390f84653bb45afb27fcb20c35347ce
Source dataset
uspto-grants-2007_04
Patent number
US07199124B2

Reaction notes

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