Hydrochloric Acid → 3-(4-tert-butyl-N-methylbenzamido)benzenesulfonic acid

HRID 79098

Reaction equation

HRID 79098 reaction equation
[H-].[Na+].[C:3]([C:7]1[CH:25]=[CH:24][C:10]([C:11]([NH:13][C:14]2[CH:15]=[C:16]([S:20]([OH:23])(=[O:22])=[O:21])[CH:17]=[CH:18][CH:19]=2)=[O:12])=[CH:9][CH:8]=1)([CH3:6])([CH3:5])[CH3:4].I[CH3:27].Cl>C1COCC1>[C:3]([C:7]1[CH:25]=[CH:24][C:10]([C:11]([N:13]([C:14]2[CH:15]=[C:16]([S:20]([OH:23])(=[O:22])=[O:21])[CH:17]=[CH:18][CH:19]=2)[CH3:27])=[O:12])=[CH:9][CH:8]=1)([CH3:6])([CH3:4])[CH3:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 589881093-(4-Tert-butylbenzamido)benzenesulfonic acid

Product 1

HCID 589880553-(4-tert-butyl-N-methylbenzamido)benzenesulfonic acidYield 23%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (26 mg, 0.66 mmol) was added to a stirred solution of 3-(4-tertbutylbenzamido)benzenesulfonic acid (0.10 g, 0.30 mmol) in THF (5 mL), and after 30 min iodomethane (37 μL, 0.60 mmol) was added. The reaction was stirred for 17 h, and 1 M aqueous hydrochloric acid (1 mL) was added. The solvent was removed under vacuum, and the residue was purified by preparative reverse phase HPLC using 10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA) to give 3-(4-tert-butyl-N-methylbenzamido)benzenesulfonic acid (24 mg, 23% yield). LC/MS: m/z 348.3 (M+H)+ at 3.82 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. customThe solvent was removed under vacuum
  2. customthe residue was purified by preparative reverse phase

Sources & evidence

ORD record
ord-f7703b6140e942eaad28dd4b9311609a
Source dataset
uspto-grants-2014_09
Patent number
US08841483B2

Linked notes

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