Hydrochloric Acid → 3-(2',4'-Dichlorobiphenyl-4-ylsulfonamido)benzoic acid

HRID 221381Notes

Reaction equation

HRID 221381 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([S:15]([NH:18][C:19]2[CH:20]=[C:21]([CH:27]=[CH:28][CH:29]=2)[C:22]([O:24]CC)=[O:23])(=[O:17])=[O:16])=[CH:11][CH:10]=1.[OH-].[Na+].Cl>C1COCC1.CO>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:10]=[CH:11][C:12]([S:15]([NH:18][C:19]2[CH:20]=[C:21]([CH:27]=[CH:28][CH:29]=2)[C:22]([OH:24])=[O:23])(=[O:16])=[O:17])=[CH:13][CH:14]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 25094972HCID 25094972, compound

Product 1

HCID 250949733-(2',4'-Dichlorobiphenyl-4-ylsulfonamido)benzoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 3-(2′,4′-dichlorobiphenyl-4-ylsulfonamido)benzoate (0.4 g) was dissolved in a mixture of THF (5 mL) and methanol (5 mL). 1 M NaOH (10 mL) was added and the mixture stirred for 3 hours at room temperature followed by 1 hour at 50° C., by which stage a clear solution had formed. Concentrated HCl was added and the precipitate collected as a white solid. The solid was dissolved in ethyl acetate and dried with Na2SO4. Evaporation gave the title compound as a white solid, recrystallised from ethyl acetate/petrol. 13C NMR (250 MHz, DMSO-d6): δ 122.4, 124.1, 125.0, 126.3, 126.5, 127.7, 129.6, 130.4, 131.9, 132.2, 132.5, 133.8, 137.1, 137.9, 138.9, 142.0 and 166.8. MS, m/z: Calcd, 420.99. Found, 421.22 (M).

Workup

  1. waitfollowed by 1 hour at 50° C., by which stage
  2. customa clear solution had formed
  3. customthe precipitate collected as a white solid
  4. dissolutionThe solid was dissolved in ethyl acetate
  5. dry with materialdried with Na2SO4
  6. customEvaporation

Sources & evidence

ORD record
ord-cfe4d6efff9340479666495a7937d84e
Source dataset
uspto-grants-2012_06
Patent number
US08207167B2

Reaction notes

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