Triethylamine → 2-bromo-N-(pyrazin-2-yl)acetamide

HRID 389910Notes

Reaction equation

HRID 389910 reaction equation
[NH2:1][C:2]1[CH:6]=CN[N:3]=1.C([N:9]([CH2:12][CH3:13])CC)C.[Br:14][CH2:15][C:16](Cl)=[O:17]>CC(C)=O>[Br:14][CH2:15][C:16]([NH:1][C:2]1[CH:6]=[N:9][CH:12]=[CH:13][N:3]=1)=[O:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 89602Bromoacetyl chlorideHCID 178418806HCID 178418806, compound

Product 1

HCID 445426692-bromo-N-(pyrazin-2-yl)acetamide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Conditions

Temperature
2.5 °C

Procedure

A stirred solution of amino pyrazole (10 g, 105 mmol) in acetone (100 ml) is treated with triethylamine (16.1 ml, 115 mmol) and then cooled to 0-5° C. using an ice bath. To the cooled solution is added drop-wise bromoacetyl chloride (8.76 g, 105 mmol) in acetone (10 ml). The cooled reaction mixture is stirred for 3 hours and then filtered. The solvent is removed in vacuo and purification by chromatography on silica (eluting with ethyl acetate-iso-hexane, 2:1 increasing to 100% ethyl acetate) affords the titled compound.

Workup

  1. customThe cooled reaction mixture
  2. filtrationfiltered
  3. customThe solvent is removed in vacuo and purification by chromatography on silica (eluting with ethyl acetate-iso-hexane, 2:1 increasing to 100% ethyl acetate)

Sources & evidence

ORD record
ord-b3fea9a964e045e2a2a95b3bbfb05a46
Source dataset
uspto-grants-2013_02
Patent number
US08383625B2

Reaction notes

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