Sodium Bicarbonate → N-(1-ethyl-2-pyrrolidinylmethyl)-2-methoxy-4-methyl-5-t-butylaminosulfonamidobenzamide

HRID 1065618Notes

Reaction equation

HRID 1065618 reaction equation
[CH2:1]([N:3]1[CH2:7][CH2:6][CH2:5][CH:4]1[CH2:8][NH:9][C:10](=[O:21])[C:11]1[CH:16]=[C:15]([NH2:17])[C:14]([CH3:18])=[CH:13][C:12]=1[O:19][CH3:20])[CH3:2].[C:22]([NH:26][S:27](Cl)(=[O:29])=[O:28])([CH3:25])([CH3:24])[CH3:23].C(=O)([O-])O.[Na+]>C(Cl)Cl.C(N(CC)CC)C>[CH2:1]([N:3]1[CH2:7][CH2:6][CH2:5][CH:4]1[CH2:8][NH:9][C:10](=[O:21])[C:11]1[CH:16]=[C:15]([NH:17][S:27]([NH:26][C:22]([CH3:25])([CH3:24])[CH3:23])(=[O:29])=[O:28])[C:14]([CH3:18])=[CH:13][C:12]=1[O:19][CH3:20])[CH3:2]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 12682606N-tert-butylsulfamoyl chlorideHCID 53707869N-(1-ethyl-2-pyrrolidinylmethyl)-2-methoxy-4-methyl-5-aminobenzamide

Product 1

HCID 12848767N-(1-ethyl-2-pyrrolidinylmethyl)-2-methoxy-4-methyl-5-t-butylaminosulfonamidobenzamideYield 68.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent3×HCID 8471TriethylamineSolvent

Procedure

To a mixture of N-(1-ethyl-2-pyrrolidinylmethyl)-2-methoxy-4-methyl-5-aminobenzamide (1.0 g), dry methylene chloride (20 ml), and triethylamine (693 mg) is added dropwise a mixture of t-butylaminosulfonyl chloride (707 mg) and methylene chloride (5 ml) with ice cooling and stirring. After stirring for 15 minutes, the reaction mixture is mixed with aqueous sodium hydrogencarbonate and shaken with methylene chloride. The organic layer is washed with water, dried over sodium sulfate, and evaporated to remove the solvent. The residue is chromatographed on a column of alumina and eluted with 0-2% methanol/methylene chloride. The eluate is recrystallized from ethyl acetate/isopropyl ether to give N-(1-ethyl-2-pyrrolidinylmethyl)-2-methoxy-4-methyl-5-t-butylaminosulfonamidobenzamide (1.0 g) as crystals melting at 167° to 168° C.

Workup

  1. additionis added dropwise
  2. stirringAfter stirring for 15 minutes
  3. washThe organic layer is washed with water
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customto remove the solvent
  7. customThe residue is chromatographed on a column of alumina
  8. washeluted with 0-2% methanol/methylene chloride
  9. customThe eluate is recrystallized from ethyl acetate/isopropyl ether

Sources & evidence

ORD record
ord-17f3c93987cc4016ae9647bcb3802ed4
Source dataset
uspto-grants-1982_05
Patent number
US04330472

Reaction notes

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