Furfurylamine → HCID 68276609, compound

HRID 1400311Notes

Reaction equation

HRID 1400311 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][NH2:7].[Br:8][C:9]([F:16])([F:15])[C:10](OCC)=[O:11].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[Br:8][C:9]([F:16])([F:15])[C:10]([NH:7][CH2:6][C:2]1[O:1][CH:5]=[CH:4][CH:3]=1)=[O:11]

Participants

6

Reactant 3

HCID 3438FurfurylamineHCID 11430Potassium CarbonateHCID 69585Ethyl bromodifluoroacetate

Product 1

HCID 68276609HCID 68276609, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(furan-2-yl)methanamine (1 g, 10.3 mmol) in 15 mL of dry DMF, ethyl bromo(difluoro)acetate (2.3 g, 11.3 mmol) and K2CO3 (2.13 g, 15.4 mmol) were added. The solution was stirred for 18 h at room temperature. The mixture was diluted with 30 mL of water and extracted with 2×20 mL of ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to afford 2-bromo-2,2-difluoro-N-(furan-2-ylmethyl)acetamide as red oil (2.3 g, 88% yield). HPLC-MS (ESI+): m/z 255.03 [M+H+].

Workup

  1. extractionextracted with 2×20 mL of ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2b8fcca4d09445f9832331aa8164cfe5
Source dataset
uspto-grants-2014_12
Patent number
US08906946B2

Reaction notes

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