Hydrochloric Acid → HCID 86731610, compound

HRID 1746444Notes

Reaction equation

HRID 1746444 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]([CH2:23][CH:24]([CH3:26])[CH3:25])[S:10]([C:13]1[CH:22]=[CH:21][C:16]([C:17]([O:19]C)=[O:18])=[CH:15][CH:14]=1)(=[O:12])=[O:11].[OH-].[Na+].Cl>O1CCCC1.O>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]([CH2:23][CH:24]([CH3:26])[CH3:25])[S:10]([C:13]1[CH:14]=[CH:15][C:16]([C:17]([OH:19])=[O:18])=[CH:21][CH:22]=1)(=[O:12])=[O:11]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86731611HCID 86731611, compound

Product 1

HCID 86731610HCID 86731610, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
110 °C

Procedure

A solution of methyl 4-(N-(2,4-dimethylphenyl)-N-isobutylsulfamoyl)benzoate (1.2698 g, 3.38 mmol) in tetrahydrofuran (THF) (8 mL) and water (2 mL), was prepared and treated with sodium hydroxide (1.015 mL, 10.15 mmol). The reaction was then heated by microwaves to 110° C., for 30 minutes. After cooling, the solution was neutralised with 2M HCl and concentrated in vacuo. The product was extracted into the organic phase of an aqueous work up between water and ethyl acetate. The organic phase was then separated (hydrophobic frit) and concentrated in vacuo to give the desired product, 1.063 g. LCMS (M+1) 362, RT 1.27 mins.

Workup

  1. temperatureAfter cooling
  2. concentrationconcentrated in vacuo
  3. extractionThe product was extracted into the organic phase of an aqueous work up between water and ethyl acetate
  4. customThe organic phase was then separated (hydrophobic frit)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-20a9466948a44f5db5ad7da4d5c0dcab
Source dataset
uspto-grants-2015_10
Patent number
US09150508B2

Reaction notes

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