Hydrochloric Acid → 3-[[2-(2-Tert-butylsulfamoyl-4-isopropylphenyl)ethyl]sulfamoyl]-4-methoxybenzamide

HRID 733367Notes

Reaction equation

HRID 733367 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([O:14][CH3:15])=[C:8]([S:10](Cl)(=[O:12])=[O:11])[CH:9]=1)(=[O:3])[NH2:2].[NH2:16][CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([CH:25]([CH3:27])[CH3:26])=[CH:21][C:20]=1[S:28]([NH:31][C:32]([CH3:35])([CH3:34])[CH3:33])(=[O:30])=[O:29].C(N(CC)CC)C.Cl>CN(C)C=O.O>[C:32]([NH:31][S:28]([C:20]1[CH:21]=[C:22]([CH:25]([CH3:26])[CH3:27])[CH:23]=[CH:24][C:19]=1[CH2:18][CH2:17][NH:16][S:10]([C:8]1[CH:9]=[C:4]([CH:5]=[CH:6][C:7]=1[O:14][CH3:15])[C:1]([NH2:2])=[O:3])(=[O:12])=[O:11])(=[O:30])=[O:29])([CH3:33])([CH3:34])[CH3:35]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 159220085-Carbamoyl-2-methoxybenzenesulfonyl chlorideHCID 178563122-(2-aminoethyl)-N-tert-butyl-5-isopropylbenzenesulfonamide

Product 1

HCID 184569453-[[2-(2-Tert-butylsulfamoyl-4-isopropylphenyl)ethyl]sulfamoyl]-4-methoxybenzamideYield 86.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of 241 mg of 5-carbamoyl-2-methoxybenzene-sulfonyl chloride and 288 mg of 2-(2-aminoethyl)-N-tert-butyl-5-isopropylbenzenesulfonamide in 10 mL of N,N-dimethyl-formamide was added 0.32 mL of triethylamine, and the mixture was stirred at room temperature for 3 days. To the reaction mixture was added 30 mL of water, and the mixture was stirred at the same temperature for 1 hour. To the mixture was added 10 mL of 1 mol/L hydrochloric acid, and the mixture was extracted three times with 20 mL of ethyl acetate. The organic layers were combined and washed with 30 mL of water, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give 426 mg of 3-[[2-(2-tert-butylsulfamoyl-4-isopropylpheyl)ethyl]sulfamoyl]-4-methoxybenzamide.

Workup

  1. stirringthe mixture was stirred at the same temperature for 1 hour
  2. extractionthe mixture was extracted three times with 20 mL of ethyl acetate
  3. washwashed with 30 mL of water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-206c150509ee4b36b96d262dda5148fd
Source dataset
uspto-grants-2009_09
Patent number
US07589126B2

Reaction notes

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