Hydrochloric Acid → HCID 68153349, compound

HRID 1405399Notes

Reaction equation

HRID 1405399 reaction equation
[CH3:1][N:2]([C:16]1[S:17][CH:18]=[CH:19][N:20]=1)[S:3]([C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12]C)=[O:11])=[CH:8][CH:7]=1)(=[O:5])=[O:4].O1CCOCC1.[OH-].[Na+].Cl>C(OCC)(=O)C>[CH3:1][N:2]([C:16]1[S:17][CH:18]=[CH:19][N:20]=1)[S:3]([C:6]1[CH:7]=[CH:8][C:9]([C:10]([OH:12])=[O:11])=[CH:14][CH:15]=1)(=[O:4])=[O:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 68153674HCID 68153674, compound

Product 1

HCID 68153349HCID 68153349, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To methyl 4-[methyl(thiazol-2-yl)sulfamoyl]benzoate (4.22 g, 13.5 mmol) and 1,4-dioxane (32 mL) was added aq. NaOH (62 mL of 2.5 M, 155 mmol) and the mixture was stirred at 50° C. for 1 hour. The reaction mixture was cooled to room temperature. Ethyl acetate (135 mL) was added before acidifying it to pH 1 with HCl (37%). The organic and aqueous layers were separated. The aqueous layer was extracted with ethyl acetate (1×50 mL). The organic layers were dried over sodium sulfate, filtered and the solvent was evaporated under reduced pressure to yield 4-[methyl(thiazol-2-yl)sulfamoyl]benzoic acid (3.63 g, 87%) as a white solid. ESI-MS m/z calc. 298.0, found 299.1 (M+1)+; Retention time: 1.31 minutes (3 minutes run). 1H NMR (400 MHz, DMSO) δ 13.56 (s, 1H), 8.14 (d, J=8.6 Hz, 2H), 7.92 (d, J=8.5 Hz, 2H), 7.46 (d, J=3.6 Hz, 1H), 7.44 (d, J=3.6 Hz, 1H), 3.39 (s, 3H).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customThe organic and aqueous layers were separated
  3. extractionThe aqueous layer was extracted with ethyl acetate (1×50 mL)
  4. dry with materialThe organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-7558462fb43a4d58b64565f59762382c
Source dataset
uspto-grants-2014_12
Patent number
US08916565B2

Reaction notes

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