4-Aminoacetanilide → HCID 59852443, compound

HRID 2373161Notes

Reaction equation

HRID 2373161 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[CH:4][CH:3]=1.C([O-])(O)=O.[Na+].[Cl:17][C:18]1[N:23]=[C:22](Cl)[CH:21]=[CH:20][N:19]=1>C1COCC1.C(O)C>[Cl:17][C:18]1[N:23]=[C:22]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[CH:6][CH:7]=2)[CH:21]=[CH:20][N:19]=1

Participants

6

Reactant 3

HCID 312304-AminoacetanilideHCID 775312,4-DichloropyrimidineHCID 516892Sodium Bicarbonate

Product 1

HCID 59852443HCID 59852443, compoundYield 96.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
85 °C

Procedure

To a stirred solution of N-(4-aminophenyl)acetamide (5 g, 0.033 mol) and NaHCO3 (5.6 g, 0.067 mol) in THF (20 mL) and ethanol (80 mL) was added 2,4-dichloropyrimidine (5.95 g, 0.04 mol) at room temperature. The reaction was gradually heated to 85° C. After the reaction was stirred for four hours at 85° C. under N2, the suspension was filtered and washed thoroughly with ethanol. The filtrate was concentrated under reduced pressure, and the resulting solid was washed with EtOAc to remove excess 2,4-dichloropyrimidine to yield 8.35 g (95.5% yield) of N-{4-[(2-chloropyrimidin-4-yl)amino]phenyl}acetamide as an off-white solid.

Workup

  1. filtrationthe suspension was filtered
  2. washwashed thoroughly with ethanol
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. washthe resulting solid was washed with EtOAc
  5. customto remove excess 2,4-dichloropyrimidine

Sources & evidence

ORD record
ord-46b221d9f10a44a0abcf4ea8d67843c1
Source dataset
uspto-grants-2008_12
Patent number
US07459455B2

Reaction notes

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