Dibutylamine → HCID 20505824, compound

HRID 1390512Notes

Reaction equation

HRID 1390512 reaction equation
[CH2:1]([NH:5][CH2:6][CH2:7][CH2:8][CH3:9])[CH2:2][CH2:3][CH3:4].[Cl:10][C:11]1[C:19]([S:20](Cl)(=[O:22])=[O:21])=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[CH:13][CH:12]=1>C(Cl)Cl>[Cl:10][C:11]1[C:19]([S:20](=[O:22])(=[O:21])[N:5]([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:1][CH2:2][CH2:3][CH3:4])=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 8148DibutylamineHCID 756134-Chloro-3-(chlorosulphonyl)benzoic acid

Product 1

HCID 20505824HCID 20505824, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3.9 g. (0.03 mole) of di-n-butylamine in 15 ml. of methylene chloride is added 2.5 g. (0.01 mole) of 4-chloro-5-chlorosulfonylbenzoic acid (J. Pharm. Pharmacol., 683 (1962), and the resulting reaction mixture allowed to stir at room temperature for 3 hrs. The solvent is removed under reduced pressure and the residue partitioned between 1N sodium hydroxide and diethyl ether. The aqueous phase is separated, acidified with 12N hydrochloric acid and the precipitated solid filtered and dried, 3.0 g., m.p. 93°-96° C. Recrystallization from ether-hexane provides the pure product, 2.5 g., m.p. 94.5°-96.5° C.

Workup

  1. custom, 683 (1962), and the resulting reaction mixture
  2. customThe solvent is removed under reduced pressure
  3. customthe residue partitioned between 1N sodium hydroxide and diethyl ether
  4. customThe aqueous phase is separated
  5. filtrationthe precipitated solid filtered
  6. customdried
  7. customRecrystallization from ether-hexane
  8. customprovides the pure product, 2.5 g

Sources & evidence

ORD record
ord-50abda334e24435f9a04cb793cde78eb
Source dataset
uspto-grants-1979_02
Patent number
US04138399

Reaction notes

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