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

HRID 988080Notes

Reaction equation

HRID 988080 reaction equation
C(N(CC)CC)C.[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][C:10]=1[S:17]([NH2:20])(=[O:19])=[O:18].[Cl:21][CH2:22][CH2:23][CH2:24][C:25](Cl)=[O:26]>O1CCCC1>[NH2:20][S:17]([C:10]1[CH:11]=[C:12]([O:15][CH3:16])[CH:13]=[CH:14][C:9]=1[NH:8][C:25](=[O:26])[CH2:24][CH2:23][CH2:22][Cl:21])(=[O:18])=[O:19]

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 are added to a solution containing 96.4 mmol of 2-amino-5-methoxybenzenesulphonamide in 200 ml of tetrahydrofuran (THF), followed dropwise by a solution containing 135 mmol of 4-chlorobutanoic acid chloride in 30 ml of THF. After stirring overnight at room temperature, the THF is removed by evaporation and the residue is taken up in water. After 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. customthe THF is removed by evaporation
  2. extractionAfter extraction with ethyl acetate
  3. washthe organic phase is washed
  4. customdried
  5. customAfter evaporation

Sources & evidence

ORD record
ord-cd05c004f85e433396a751d84c46e736
Source dataset
uspto-grants-2003_10
Patent number
US06635635B2

Reaction notes

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