Acetyl chloride → HCID 117667771, compound

HRID 712635Notes

Reaction equation

HRID 712635 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH2:8][NH2:9].C([O-])([O-])=O.[Na+].[Na+].[C:16](Cl)(=[O:18])[CH3:17]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH2:8][NH:9][C:16](=[O:18])[CH3:17]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 10340Sodium CarbonateHCID 469079661-(3-Bromopyridin-4-yl)methanamine

Product 1

HCID 117667771HCID 117667771, compoundYield 48.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (3-bromopyridin-4-yl) methanamine (3.5 g, 19 mmol) in DCM (880 mL) is added Na2CO3 (3.0 g, 28 mmol), then acetyl chloride (1.6 g, 21 mmol) is added at 0° C. under N2 atmosphere. The mixture is stirred at room temperature for 3 hrs and then it is diluted with DCM. The mixture is washed with water and brine, dried over Na2SO4, filtered and concentrated to give the crude product. Purification by flash column chromatography affords 2.1 g of N-(3-Bromo-pyridin-4-ylmethyl)-acetamide.

Workup

  1. washThe mixture is washed with water and brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give the crude product
  6. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-25a7983031df4a4f82cd2c059851a1ca
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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