Propylamine → HCID 22169334, compound

HRID 1822622Notes

Reaction equation

HRID 1822622 reaction equation
[CH2:1]([NH2:4])[CH2:2][CH3:3].[F:5][C:6]([F:21])([S:17](F)(=[O:19])=[O:18])[C:7]([F:16])([F:15])[C:8]([F:14])([F:13])[C:9]([F:12])([F:11])[F:10]>C(OCC)(=O)C>[CH2:1]([NH:4][S:17]([C:6]([F:5])([F:21])[C:7]([F:15])([F:16])[C:8]([F:13])([F:14])[C:9]([F:12])([F:11])[F:10])(=[O:19])=[O:18])[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 7852PropylamineHCID 67814Perfluoro-1-butanesulfonyl fluoride

Product 1

HCID 22169334HCID 22169334, compoundYield 91.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

n-Propylamine (26.60 g) and ethyl acetate (120 mL) were placed in a glass flask equipped with a stirrer, a condenser and a thermometer, and perfluorobutansulfonyl fluoride (available from Azumax Company) (45.31 g) was added dropwise over 1 hour using a dropping funnel to the flask in an ice bath. After completion of the dropping, the mixture in the flask was heated at 40□ with an oil bath and the mixture was stirred for 5 hours. Then the mixture was cooled to the room temperature and was washed twice with 75 ml of 9% aq. hydrochloric acid solution. Ethyl acetate layer was dried with magnesium sulfate and then was filtered off. Ethyl acetate was evaporated under vacuum to obtain N-propylperfluorobutanesulfonamide (46.8 g).

Workup

  1. customequipped with a stirrer, a condenser
  2. temperatureAfter completion of the dropping, the mixture in the flask was heated at 40□ with an oil bath
  3. washwas washed twice with 75 ml of 9% aq. hydrochloric acid solution
  4. dry with materialEthyl acetate layer was dried with magnesium sulfate
  5. filtrationwas filtered off
  6. customEthyl acetate was evaporated under vacuum

Sources & evidence

ORD record
ord-8bb18708bf9e4d2799546758ef560ae3
Source dataset
uspto-grants-2006_05
Patent number
US07037636B2

Reaction notes

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