Methyl 5-(chlorosulfonyl)-2-hydroxybenzoate → methyl 5-(N-(4-ethylphenyl)-N-isobutylsulfamoyl)-2-hydroxybenzoate

HRID 1487087Notes

Reaction equation

HRID 1487087 reaction equation
[CH2:1]([C:3]1[CH:13]=[CH:12][C:6]([NH:7][CH2:8][CH:9]([CH3:11])[CH3:10])=[CH:5][CH:4]=1)[CH3:2].Cl[S:15]([C:18]1[CH:19]=[CH:20][C:21]([OH:28])=[C:22]([CH:27]=1)[C:23]([O:25][CH3:26])=[O:24])(=[O:17])=[O:16]>N1C=CC=CC=1>[CH2:1]([C:3]1[CH:13]=[CH:12][C:6]([N:7]([CH2:8][CH:9]([CH3:10])[CH3:11])[S:15]([C:18]2[CH:19]=[CH:20][C:21]([OH:28])=[C:22]([CH:27]=2)[C:23]([O:25][CH3:26])=[O:24])(=[O:17])=[O:16])=[CH:5][CH:4]=1)[CH3:2]

Participants

4

Reactant 2

HCID 12581955Methyl 5-(chlorosulfonyl)-2-hydroxybenzoateHCID 284793854-ethyl-N-(2-methylpropyl)aniline

Product 1

HCID 89875692methyl 5-(N-(4-ethylphenyl)-N-isobutylsulfamoyl)-2-hydroxybenzoate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 4-ethyl-N-isobutylaniline (598 mg, 3.37 mmol) in pyridine (10 mL) stirred in air at 20° C., was added methyl 5-(chlorosulfonyl)-2-hydroxybenzoate (845 mg, 3.37 mmol) portionwise, over 1 hour. The reaction mixture was then stirred at 20° C. for 30 minutes. The solvent was evaporated in vacuo to give the crude product as a yellow sticky solid. This was triturated with methanol then filtered and dried to give the title product as a white solid, 907 mg. LCMS [LCMS1] Rt 1.38 min, m/z (ES+) 392 (M+H).

Workup

  1. customThe solvent was evaporated in vacuo
  2. customto give the crude product as a yellow sticky solid
  3. customThis was triturated with methanol
  4. filtrationthen filtered
  5. customdried

Sources & evidence

ORD record
ord-1c95b7443be343bf8ff1a8af3ec77385
Source dataset
uspto-grants-2016_08
Patent number
US09428452B2

Reaction notes

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