Sulfuric Acid → 2-{[3-tert-butyl-1-(2-methylphenyl)-1H-pyrazol-5-yl]amino}benzenesulfonamide

HRID 915603Notes

Reaction equation

HRID 915603 reaction equation
C([N:8](CC1C=CC=CC=1)[S:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[NH:18][C:19]1[N:23]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[CH3:30])[N:22]=[C:21]([C:31]([CH3:34])([CH3:33])[CH3:32])[CH:20]=1)(=[O:11])=[O:10])C1C=CC=CC=1.OS(O)(=O)=O.[OH-].[Na+]>>[C:31]([C:21]1[CH:20]=[C:19]([NH:18][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[S:9]([NH2:8])(=[O:10])=[O:11])[N:23]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[CH3:30])[N:22]=1)([CH3:34])([CH3:33])[CH3:32]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 58958594N,N-dibenzyl-2-{[3-tert-butyl-1-(2-methylphenyl)-1H-pyrazol-5-yl]amino}benzenesulfonamide

Product 1

HCID 589585812-{[3-tert-butyl-1-(2-methylphenyl)-1H-pyrazol-5-yl]amino}benzenesulfonamideYield 64.4%

Procedure

N,N-Dibenzyl-2-{[3-tert-butyl-1-(2-methylphenyl)-1H-pyrazol-5-yl]amino}benzene-sulfonamide (from Step 2, 240 mg, 0.42 mmol) was added to conc H2SO4 (3 mL), and the mixture was vigorously stirred for 20 min. The mixture was poured onto ice, and conc NaOH solution was added until a pH of ˜7.5 was reached. The aqueous layer was extracted 2× with EtOAc, and the combined organic layers were dried with Na2SO4, filtered, and concentrated under reduced pressure. Purification by silica gel flash chromatography using EtOAc/hexane (1:3, v/v) afforded the title compound as a white solid (104 mg, 64%). 1H NMR (δ 400 MHz, CD2Cl2) 61.39 (s, 9H), 2.09 (s, 3H), 4.50 (br, 2H), 6.20 (s, 1H), 7.94 (t, 1H), 7.23 (m, 4H), 7.34 (m, 2H), 7.45 (t, 1H), 7.73 (d, 1H). ES-MS m/z 385.2 (MH+); HPLC RT (min) 3.11.

Workup

  1. additionwas added until a pH of ˜7.5
  2. extractionThe aqueous layer was extracted 2× with EtOAc
  3. dry with materialthe combined organic layers were dried with Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customPurification by silica gel flash chromatography

Sources & evidence

ORD record
ord-46b46d649cfd424b97038400a8acb54f
Source dataset
uspto-grants-2007_09
Patent number
US07265144B2

Reaction notes

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