Pyridine → N-(5-tert-Butyl-2-p-tolyl-2H-pyrazol-3-yl)-2-chloro-acetamide

HRID 1041907Notes

Reaction equation

HRID 1041907 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([NH2:17])[N:8]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)[N:9]=1)([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.[Cl:24][CH2:25][C:26](Cl)=[O:27]>C(Cl)Cl.C(=O)(O)[O-].[Na+]>[C:1]([C:5]1[CH:6]=[C:7]([NH:17][C:26](=[O:27])[CH2:25][Cl:24])[N:8]([C:10]2[CH:11]=[CH:12][C:13]([CH3:16])=[CH:14][CH:15]=2)[N:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 1049PyridineHCID 6577Chloroacetyl chlorideHCID 29741323-tert-butyl-1-(4-methylphenyl)-1H-pyrazol-5-amine

Product 1

HCID 66977571N-(5-tert-Butyl-2-p-tolyl-2H-pyrazol-3-yl)-2-chloro-acetamideYield 100%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

A solution of 5-tert-butyl-2-p-tolyl-2H-pyrazol-3-ylamine (886 mg, 3.86 mmol), pyridine (465 μL, 5.80 mmol) and chloroacetyl chloride (462 μL, 5.80 mmol) in DCM (5 mL) was stirred at RT for 2 h. The reaction mixture was diluted with aq. sat. sodium bicarbonate and DCM and the resulting aqueous layer was extracted twice with DCM. The combined organic layers were dried (MgSO4) and concentrated in vacuo to afford the title compound (1.17 g, 100%) as a yellow solid. LCMS (Method 5): Rt 4.41 min, m/z 306 [MH+].

Workup

  1. extractionthe resulting aqueous layer was extracted twice with DCM
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c6142b03d4e8488699e853c9f6351274
Source dataset
uspto-grants-2013_10
Patent number
US08557797B2

Reaction notes

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