Triethylamine → N-[2-(Aminosulphonyl)4-methoxyphenyl]-4-chlorobutanamide

HRID 851875Notes

Reaction equation

HRID 851875 reaction equation
C(N(CC)CC)C.[Cl:8][CH2:9][CH2:10][CH2:11][C:12](Cl)=[O:13].[NH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][C:17]=1[S:24]([NH2:27])(=[O:26])=[O:25]>O1CCCC1>[NH2:27][S:24]([C:17]1[CH:18]=[C:19]([O:22][CH3:23])[CH:20]=[CH:21][C:16]=1[NH:15][C:12](=[O:13])[CH2:11][CH2:10][CH2:9][Cl:8])(=[O:25])=[O:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 783704-Chlorobutyryl chlorideHCID 112526652-Amino-5-methoxybenzenesulfonamide

Product 1

HCID 15908218N-[2-(Aminosulphonyl)4-methoxyphenyl]-4-chlorobutanamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

144 mmol of triethylamine and then, dropwise, a solution containing 135 mmol of 4-chlorobutanoic acid chloride in 30 ml of tetrahydrofuran (THF), are added to a solution containing 96.4 mmol of 2-amino-5-methoxybenzenesulphonamide in 200 ml of THF. After stirring overnight at ambient temperature, the THF is evaporated off and the residue is taken up in water. Following extraction with ethyl acetate, the organic phase is washed and dried. After evaporation, the expected product is obtained in the form of an oil.

Workup

  1. additionare added to a solution
  2. customthe THF is evaporated off
  3. extractionextraction with ethyl acetate
  4. washthe organic phase is washed
  5. customdried
  6. customAfter evaporation

Sources & evidence

ORD record
ord-dfdf212ed3e34cef8c7f22471cfe2e7b
Source dataset
uspto-grants-2007_08
Patent number
US07253161B2

Reaction notes

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