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

HRID 1730144Notes

Reaction equation

HRID 1730144 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.[NH2:8][C:9]1[N:14]=[C:13]([Cl:15])[CH:12]=[C:11]([Cl:16])[N:10]=1.C(Cl)(=O)C>>[C:5]([NH:8][C:9]1[N:14]=[C:13]([Cl:15])[CH:12]=[C:11]([Cl:16])[N:10]=1)(=[O:7])[CH3:6]

Participants

4

Reactant 3

HCID 6367Acetyl chlorideHCID 7918Acetic AnhydrideHCID 655222-Amino-4,6-dichloropyrimidine

Product 1

HCID 12611964N-(4,6-Dichloropyrimidin-2-yl)acetamide

Conditions

Temperature
110 °C

Procedure

A 250 ml. three necked flask was fitted with a mechanical stirrer and a reflux condenser with drying tube. The flask is charged with 50 ml. of acetic anhydride and 3.85 g of 2-amino-4,6-dichloropyrimidine (0.025 mole). Then, 10 ml. of acetyl chloride was added slowly and the mixture was heated to 110° C for 8 hours. The mixture was allowed to stand overnight at room temperature. The crystalline solid product which formed was filtered and washed with water and sodium bicarbonate solution. It was then recrystallized from 50% alcohol. There was obtained 3.8 g of 2-acetamido-4,6-dichloropyrimidine (PY-25) in the form of white crystals, melting point, 198°-200° C, yield, 74.5%.

Workup

  1. customthree necked flask was fitted with a mechanical stirrer and a reflux condenser
  2. customwith drying tube
  3. additionThe flask is charged with 50 ml
  4. customThe crystalline solid product which formed
  5. filtrationwas filtered
  6. washwashed with water and sodium bicarbonate solution
  7. customIt was then recrystallized from 50% alcohol

Sources & evidence

ORD record
ord-d9a1175b5f344b87b702f550625511ad
Source dataset
uspto-grants-1976_11
Patent number
US03991190

Reaction notes

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