3-Methylbenzoyl chloride → N-(6-chloropyrazin-2-yl)-3-methylbenzamide

HRID 240496Notes

Reaction equation

HRID 240496 reaction equation
[NH2:1][C:2]1[CH:7]=[N:6][CH:5]=[C:4]([Cl:8])[N:3]=1.[CH3:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=1)[C:13](Cl)=[O:14]>N1C=CC=CC=1>[Cl:8][C:4]1[N:3]=[C:2]([NH:1][C:13](=[O:14])[C:12]2[CH:16]=[CH:17][CH:18]=[C:10]([CH3:9])[CH:11]=2)[CH:7]=[N:6][CH:5]=1

Participants

4

Reactant 2

HCID 743753-Methylbenzoyl chlorideHCID 1184582-Amino-6-Chloropyrazine

Product 1

HCID 86635811N-(6-chloropyrazin-2-yl)-3-methylbenzamideYield 97%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

2-Amino-6-chloropyrazine (496.0 mg, 3.83 mmol) was dissolved in pyridine (15 mL). 3-Methylbenzoyl chloride (760 μL, 5.77 mmol) was added to the reaction mixture. The reaction was heated to 100° C. for 16 h then concentrated under vacuum. The residue was partitioned between 1M K2CO3 (50 mL) and CH2Cl2 (4×50 mL). The organic extracts were combined, washed with and brine (50 mL), dried over Na2SO4, filtered and concentrated under vacuum. The residue was purified by silica gel chromatography (5% EtOAc in CH2Cl2, Rf=0.39) to afford the title compound as a white solid (919.0 mg, 97%). MS m/z 248 (M+H)+.

Workup

  1. concentrationthen concentrated under vacuum
  2. customThe residue was partitioned between 1M K2CO3 (50 mL) and CH2Cl2 (4×50 mL)
  3. washwashed with and brine (50 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by silica gel chromatography (5% EtOAc in CH2Cl2, Rf=0.39)

Sources & evidence

ORD record
ord-1e8b1ca18c374741bfc70de23339413b
Source dataset
uspto-grants-2014_02
Patent number
US08648084B2

Reaction notes

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