1,1'-Carbonyldiimidazole → 2-(6-Chloropyridin-3-YL)acetamide

HRID 76146Notes

Reaction equation

HRID 76146 reaction equation
[CH:1]1[C:6]([CH2:7][C:8](O)=[O:9])=[CH:5][N:4]=[C:3]([Cl:11])[CH:2]=1.C1N=C[N:14](C(N2C=NC=C2)=O)C=1>C1COCC1>[Cl:11][C:3]1[N:4]=[CH:5][C:6]([CH2:7][C:8]([NH2:14])=[O:9])=[CH:1][CH:2]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 140715712-(6-Chloropyridin-3-yl)acetic acid

Product 1

HCID 532788782-(6-Chloropyridin-3-YL)acetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

To 10.0 g (58.3 mmol) (2-chloropyridyl)-5-acetic acid in 150 mL THF are added 9.45 g (58.3 mmol) CDI and the mixture is stirred at 45° C. for 1 h. Then 28.0 g (291 mmol) NH4CO3 are added and the mixture is stirred at r.t. over night. The reaction mixture is poured onto water and extracted with EtOAc. The organic layer is dried with MgSO4 and the solvent is removed in vacuo. The residue is triturated with TBME and recrystallized from EtOH.

Workup

  1. stirringthe mixture is stirred at r.t. over night
  2. additionThe reaction mixture is poured onto water
  3. extractionextracted with EtOAc
  4. dry with materialThe organic layer is dried with MgSO4
  5. customthe solvent is removed in vacuo
  6. customThe residue is triturated with TBME
  7. customrecrystallized from EtOH

Sources & evidence

ORD record
ord-53fac80ad30f443f94e8711e52839888
Source dataset
uspto-grants-2014_09
Patent number
US08835472B2

Reaction notes

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