Acetyl chloride → HCID 59578607, compound

HRID 1484506Notes

Reaction equation

HRID 1484506 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[C:9](Cl)(=[O:11])[CH3:10]>C(Cl)Cl>[Cl:8][C:5]1[N:6]=[CH:7][C:2]([NH:1][C:9](=[O:11])[CH3:10])=[CH:3][N:4]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 122159932-Chloropyrimidin-5-amine

Product 1

HCID 59578607HCID 59578607, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

5-amino-2-chloro pyrimidine (260 mg, 2 mmol) was dissolved in DCM (5 ml), TEA (0.557 ml, 4 mmol) was added and the reaction mixture was stirred at 0° C. for 15 min. Acetyl chloride (0.213 ml, 3 mmol) was added dropwise at 0° C. and the reaction mixture was stirred for 45 min. The reaction was quenched with an aqueous saturated solution of NaHCO3. The phases were separated and the aqueous phase was basified by adding solid K2CO3 while the pH was allowed to reach ˜9-10 and extracted with dichloromethane. Combined organic phases were dried over Na2SO4 and evaporated in vacuo to afford N-(2-chloropyrimidin-5-yl)acetamide (340 mg) as a crude product.

Workup

  1. stirringthe reaction mixture was stirred for 45 min
  2. customThe reaction was quenched with an aqueous saturated solution of NaHCO3
  3. customThe phases were separated
  4. additionby adding solid K2CO3 while the pH
  5. extractionextracted with dichloromethane
  6. dry with materialCombined organic phases were dried over Na2SO4
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-cb2b23625bee458ca5e7221ba7b5dd12
Source dataset
uspto-grants-2016_08
Patent number
US09422252B2

Reaction notes

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