Water → N-(4,6-Dichloropyrimidin-2-yl)acetamide

HRID 476360Notes

Reaction equation

HRID 476360 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([NH2:9])[N:3]=1.[C:10](Cl)(=[O:12])[CH3:11].O>C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([NH:9][C:10](=[O:12])[CH3:11])[N:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6367Acetyl chlorideHCID 655222-Amino-4,6-dichloropyrimidine

Product 1

HCID 12611964N-(4,6-Dichloropyrimidin-2-yl)acetamideYield 80.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 4,6-dichloro-pyrimidin-2-ylamine (5 g, 30 mmol) and acetyl chloride (4.7 g, 60 mmol) in acetic acid (200 mL) was stirred at 80° C. under nitrogen overnight. The solution was cooled to RT and water (150 mL) was added. The mixture was extracted with ethyl acetate (3×150 mL), and the combined organics were washed with brine, dried over sodium sulfate and concentrated to give N-(4,6-dichloro-pyrimidin-2-yl)-acetamide (5.0 g, 79% yield).

Workup

  1. extractionThe mixture was extracted with ethyl acetate (3×150 mL)
  2. washthe combined organics were washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4982874cf4894a52b2a3362aed23f14a
Source dataset
uspto-grants-2014_01
Patent number
US08637672B2

Reaction notes

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