4-ethyl-N-(2-methylpropyl)aniline → methyl 2-bromo-5-(N-(4-ethylphenyl)-N-isobutylsulfamoyl)benzoate

HRID 1487083Notes

Reaction equation

HRID 1487083 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].[Br:14][C:15]1[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][C:16]=1[C:17]([O:19][CH3:20])=[O:18]>N1C=CC=CC=1>[Br:14][C:15]1[CH:24]=[CH:23][C:22]([S:25](=[O:27])(=[O:26])[N:7]([C:6]2[CH:12]=[CH:13][C:3]([CH2:1][CH3:2])=[CH:4][CH:5]=2)[CH2:8][CH:9]([CH3:10])[CH3:11])=[CH:21][C:16]=1[C:17]([O:19][CH3:20])=[O:18]

Participants

4

Reactant 2

HCID 284793854-ethyl-N-(2-methylpropyl)anilineHCID 43436744Methyl 2-bromo-5-(chlorosulfonyl)benzoate

Product 1

HCID 86731597methyl 2-bromo-5-(N-(4-ethylphenyl)-N-isobutylsulfamoyl)benzoate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 4-ethyl-N-isobutylaniline (400 mg, 2.256 mmol) in pyridine (2 mL) stirred in air at 20° C. was added methyl 2-bromo-5-(chlorosulfonyl)benzoate (707 mg, 2.256 mmol) portionwise, over 30 minutes. The reaction mixture was stirred at 20° C. for 30 minutes, then left to stand overnight. The solvent was evaporated in vacuo to give the crude product as a sticky yellow solid. This was triturated with methanol and filtered and dried to give the desired product as a white solid, 600 mg. LCMS [LCMS1] Rt 1.41 min, m/z (ES+) 454/456 (M+H).

Workup

  1. waitleft
  2. waitto stand overnight
  3. customThe solvent was evaporated in vacuo
  4. customto give the crude product as a sticky yellow solid
  5. customThis was triturated with methanol
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-696967e15b9d4d1eb80752503ca9a2da
Source dataset
uspto-grants-2016_08
Patent number
US09428452B2

Reaction notes

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