Dibutylamine → HCID 20505824, compound

HRID 355141Notes

Reaction equation

HRID 355141 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 1 N sodium hydroxide and diethyl ether. The aqueous phase is separated, acidified with 12 N 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 1 N 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-d72a135ac3a14b39a2a7bdeada7e4f59
Source dataset
uspto-grants-1983_03
Patent number
US04377521

Reaction notes

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