Hydrochloric Acid → HCID 86731608, compound

HRID 1746443Notes

Reaction equation

HRID 1746443 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]([CH2:24][CH:25]([CH3:27])[CH3:26])[S:10]([C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20]([O:22]C)=[O:21])=[CH:15][CH:14]=1)(=[O:12])=[O:11].[OH-].[Na+].Cl>O1CCCC1.O.C(OCC)(=O)C>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]([CH2:24][CH:25]([CH3:27])[CH3:26])[S:10]([C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20]([OH:22])=[O:21])=[CH:15][CH:14]=1)(=[O:12])=[O:11]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86731609HCID 86731609, compound

Product 1

HCID 86731608HCID 86731608, compoundYield 98.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

A solution of methyl 2-(4-(N-(2,4-dimethylphenyl)-N-isobutylsulfamoyl)phenyl)acetate (1.3799 g, 3.54 mmol) in tetrahydrofuran (THF) (8 mL) and water (2 mL), was prepared and treated with sodium hydroxide (1.063 mL, 10.63 mmol). The reaction was then heated by microwaves to 110° C., for 30 minutes. After cooling, crude material from a test of the above reaction run on a smaller scale (˜40 mg) was combined with this mixture. The combined solution was then neutralised with 2M HCl and diluted with further water and ethyl acetate. The product was extracted into the organic phase and the organics separated (hydrophobic frit) then concentrated in vacuo to provide 1.3033 g of desired material. LCMS (M+1) 376, RT 1.24 mins.

Workup

  1. temperatureAfter cooling
  2. customcrude material from a test of the above reaction
  3. extractionThe product was extracted into the organic phase
  4. customthe organics separated (hydrophobic frit)
  5. concentrationthen concentrated in vacuo

Sources & evidence

ORD record
ord-650a6f2e61614c2890f0c0d4fce9ccfa
Source dataset
uspto-grants-2015_10
Patent number
US09150508B2

Reaction notes

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