Acetyl chloride → N-(6-chloropyrazin-2-yl)acetamide

HRID 2170196Notes

Reaction equation

HRID 2170196 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[N:4][CH:3]=1.[C:9](Cl)(=[O:11])[CH3:10]>C(Cl)Cl.O>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:9](=[O:11])[CH3:10])[CH:5]=[N:4][CH:3]=1

Participants

5

Reactant 2

HCID 6367Acetyl chlorideHCID 1184582-Amino-6-Chloropyrazine

Product 1

HCID 14787673N-(6-chloropyrazin-2-yl)acetamideYield 52.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-chloropyrazin-2-amine (1.00 g, 7.72 mmol) in DCM (20 mL) was added acetyl chloride (0.659 mL, 9.26 mmol) at RT and the reaction mixture was stirred for 1 h. The reaction mixture was diluted with water (100 mL) and extracted with DCM (2×100 mL). The combined organic layer was dried over sodium sulfate, filtered and evaporated under reduced pressure to give a residue which was purified by CombiFlash (REDISEP®, silica gel, 12 g, 25% EtOAc/petroleum ether) to give N-(6-chloropyrazin-2-yl)acetamide (0.700 g, 52.9%). LCMS Condition B-39: retention time 1.67 min, [M+1]=170.0. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.14 (s, 3H), 8.47 (s, 1H), 9.29 (s, 1H), 11.09 (br s, 1H).

Workup

  1. extractionextracted with DCM (2×100 mL)
  2. dry with materialThe combined organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customto give a residue which
  6. customwas purified by CombiFlash (REDISEP®, silica gel, 12 g, 25% EtOAc/petroleum ether)

Sources & evidence

ORD record
ord-0be256672ab646c98b82661c1fb4a21a
Source dataset
uspto-grants-2015_06
Patent number
US09050345B2

Reaction notes

Loading…