Hydrochloric Acid → 4-Phenylsulfonamidocarbonyl-2,6-dimethyl-benzoic acid

HRID 345226Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[C:6]([C:8]([OH:10])=O)[CH:5]=[C:4]([CH3:11])[C:3]=1[C:12]([OH:14])=[O:13].[C:15]1([S:21]([NH2:24])(=[O:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.CCN=C=NCCCN(C)C.Cl>CN(C=O)C>[C:15]1([S:21]([NH:24][C:8]([C:6]2[CH:5]=[C:4]([CH3:11])[C:3]([C:12]([OH:14])=[O:13])=[C:2]([CH3:1])[CH:7]=2)=[O:10])(=[O:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

Conditions

Temperature: 0 °C

Procedure

2,6-Dimethyl-1,4-benzenedicarboxylic acid (from Preparation 7) (500 mg, 2.6 mmol) and benzene sulfonamide (486 mg, 3.1 mmol) were combined in dry DMF (25 mL), and EDCI (494 mg, 2.6 mmol) was then added with stirring at 0° C. The mixture was stirred for 2 hours at 0° C. and 2 days at room temperature, then 1 N HCl (10 mL) was added, and the mixture was extracted with ethyl acetate. The organic phase was washed with 1 N HCl (1×), water (5×), and brine (3×); dried (Na2SO4); and rotary evaporated to give the crude product (used as such in the next step) as a white solid; NMR (acetone-d6) showed 8.0-7.4 ppm (multiplet with a singlet at 7.7 ppm, 7H) and 2.4 ppm (singlet, 6H).

Workup

stirringThe mixture was stirred for 2 hours at 0° C. and 2 days at room temperature
extractionthe mixture was extracted with ethyl acetate
washThe organic phase was washed with 1 N HCl (1×), water (5×), and brine (3×)
dry with materialdried (Na2SO4)
customand rotary evaporated

Sources & evidence

ORD record: ord-801c189863df4da2a21c7f064b79c7ee
Source dataset: uspto-grants-1991_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05055451

Reaction notes

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