Hydrochloric Acid → HCID 178427774, compound

HRID 2239989Notes

Reaction equation

HRID 2239989 reaction equation
[NH2:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][CH2:7][CH2:8][O:9][S:10]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)(=[O:12])=[O:11])=[CH:4][C:3]=1[CH2:22][S:23]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)(=[O:25])=[O:24].Cl.[N:33]([O-])=O.[Na+].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.O>[C:26]1([S:23]([C:22]2[C:3]3[C:2](=[CH:21][CH:20]=[C:5]([O:6][CH2:7][CH2:8][O:9][S:10]([C:13]4[CH:14]=[CH:15][C:16]([CH3:19])=[CH:17][CH:18]=4)(=[O:11])=[O:12])[CH:4]=3)[NH:1][N:33]=2)(=[O:24])=[O:25])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 23668193Sodium NitriteHCID 58812092HCID 58812092, compound

Product 1

HCID 178427774HCID 178427774, compoundYield 79.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a mixture of toluene-4-sulfonic acid 2-(4-amino-3-benzenesulfonylmethyl-phenoxy)-ethyl ester (11.7 g, 25.3 mmol) of in ethanol (350 mL) and 1.0 N hydrochloric acid (425 mL) was dropwise added sodium nitrite (2.67 g, 38.7 mmol) in water (50 mL). After stirring at ambient temperature for 1.5 hours, solid sodium carbonate was added to basic pH. The reaction mixture was stirred for an additional 2 hours. It was then solvent evaporated and extracted with warm ethyl acetate. The organic phase was washed with water and brine, dried with anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by flash chromatography with 2% methanol in chloroform to yield toluene-4-sulfonic acid 2-(3-benzenesulfonyl-1H-indazol-5-yloxy)-ethyl ester as an orange solid (9.54 g, 79.5%): MP: 174-7° C.; Mass Spectrum (−EI, [M−H]−) m/z 471. 1HNMR (500 MHz, DMSO-d6): δ14.11 (s, 1H), 7.96-7.98 (m, 2H), 7.74-7.77 (m, 2H), 7.62-7.66 (m, 1H), 7.53-7.59 (m, 3H), 7.39 (d, 2H, J=8.05 Hz), 7.24 (d, 1H, J=2.32 Hz), 6.97-7.00 (m, 1H), 4.35-4.37 (m, 2H), 4.21-4.23 (m, 2H), 2.33 ppm (s, 3H).

Workup

  1. stirringThe reaction mixture was stirred for an additional 2 hours
  2. customsolvent evaporated
  3. extractionextracted with warm ethyl acetate
  4. washThe organic phase was washed with water and brine
  5. dry with materialdried with anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography with 2% methanol in chloroform

Sources & evidence

ORD record
ord-59e7f25dc2384bba98589d13a2cd5336
Source dataset
uspto-grants-2010_05
Patent number
US07723329B2

Reaction notes

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