Butylamine → 2,6-Dichlorobenzoic acid

HRID 1602777Notes

Reaction equation

HRID 1602777 reaction equation
ClS([C:5]1[C:6]([Cl:15])=[C:7]([C:11]([Cl:14])=[CH:12][CH:13]=1)[C:8]([OH:10])=[O:9])(=O)=O.C([O-])([O-])=O.[K+].[K+].C(N)CCC>C1(C)C=CC=CC=1.Cl>[Cl:14][C:11]1[CH:12]=[CH:13][CH:5]=[C:6]([Cl:15])[C:7]=1[C:8]([OH:10])=[O:9]

Participants

6

Reactant 3

HCID 8007ButylamineHCID 11430Potassium CarbonateHCID 35382162,6-dichloro-3-chlorosulfonyl-benzoic Acid

Product 1

HCID 57582,6-Dichlorobenzoic acid

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 1140TolueneSolvent

Conditions

Temperature
25 °C

Procedure

Part B: 3-(Chlorosulfonyl)-2,6-dichlorobenzoic acid (1.5 g; 5.2 mmol) was dissolved in anhydrous toluene (35 ml) to which was added powdered K2CO3 (1.44 g: 10.4 mmol) and n-butylamine (1.0 ml, 10.4 mmol). The reaction mixture was stirred at 25° C. for 12 hours. The solution was diluted slowly with 1 M ethereal HCl (20 ml) and was then stirred for 30 minutes. The solution was filtered and the resulting filtrate was evaporated to dryness to give crude product. Further purification of the material by silica gel chromatography using EtOAc as the eluent provided 3-N-butylsulfonamidoyl)-2,6-dichlorobenzoic acid (Formula 3) (1.43 g, 85%. 1H NMR (DMSO) d 8.11 (t, 1H), 7.98 and 7.71 (doublets, 1H each), 2.75 (m, 2H), 1.55 (m, 2H), 1.32 (m 2H), 0.87 (t, 3H)

Workup

  1. stirringwas then stirred for 30 minutes
  2. filtrationThe solution was filtered
  3. customthe resulting filtrate was evaporated to dryness
  4. customto give crude product
  5. customFurther purification of the material by silica gel chromatography

Sources & evidence

ORD record
ord-e6357cf367944029b7e2254e2f3077e7
Source dataset
uspto-grants-1999_11
Patent number
US05985838

Reaction notes

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