4-Fluorobenzenesulfonyl chloride → HCID 20066969, compound

HRID 358642Notes

Reaction equation

HRID 358642 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([OH:11])=[O:10].[F:12][C:13]1[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1.[OH-].[Na+]>O.[OH-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>[F:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([OH:11])=[O:10])(=[O:21])=[O:20])=[CH:15][CH:14]=1

Participants

7

Reactant 3

HCID 95884-Fluorobenzenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 660858-Aminooctanoic acid

Product 1

HCID 20066969HCID 20066969, compoundYield 46.2%

Reagents, catalysts & solvents 3

HCID 2723671Tetrabutylammonium HydroxideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

8-Aminooctanoic acid (1.0 g, 0.006 mol) was treated with 4-fluorobenzenesulphonyl chloride (1.22 g, 0.006 mol) in the presence of sodium hydroxide (0.8 g, 0.019 mol) in 15 ml water, tetrabutylammonium hydroxide (4 drops, 40% solution) and dichloromethane and the resulting mixture was subjected to vigorous stirring for 3 hours. The organic layer was then separated and evaporated to dryness and the residue was recrystallised from 2-propanol-water to give the title compound (0.88 g, m.p. 97°-8° C.).

Workup

  1. customThe organic layer was then separated
  2. customevaporated to dryness
  3. customthe residue was recrystallised from 2-propanol-water

Sources & evidence

ORD record
ord-39931d8fef49444ba8c790dfb17e2dbc
Source dataset
uspto-grants-1991_03
Patent number
US04997847

Reaction notes

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