Triethylamine → Benzamide

HRID 1703159Notes

Reaction equation

HRID 1703159 reaction equation
C(N1CCCC1C[NH:9][C:10](=[O:25])[C:11]1[CH:16]=[C:15](NS(C)(=O)=O)[C:14](C)=[CH:13][C:12]=1OC)C.C(N(CC)CC)C.CN(C)S(Cl)(=O)=O>C(Cl)Cl>[C:10]([NH2:9])(=[O:25])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5011568256-07-5HCID 83372Dimethylsulphamoyl chloride

Product 1

HCID 2331BenzamideYield 214.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of N-(1-ethyl-2-pyrrolidinylmethyl)-2-methoxy-4-methyl-5-methanesulfonamidobenzamide (500 mg), triethylamine (823 mg), dimethylaminosulfonyl chloride (1.17 g), and methylene chloride (20 ml) is refluxed for 39 hours. The reaction mixture is washed with aqueous sodium hydrogencarbonate. 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 0.5-1% methanol/methylene chloride. The eluate is evaporated to give N-(1-ethyl-2-pyrrolidinylmethyl)-2-methoxy-4-methyl-5-[N-(dimethylaminosulfonyl)-methanesulfonamido[benzamide (351 mg) as an oil. This product is mixed with tetrahydrofuran (3 ml) and 10% sodium hydroxide (3 ml) and warmed at 80° C. for 1 hour. The reaction mixture is evaporated to remove the tetrahydrofuran, acidified with hydrochloric acid, made alkaline with sodium hydrogencarbonate, salted out with sodium chloride, and shaken with methylene chloride. The organic layer is washed with saturated brine, dried over sodium sulfate, and evaporated to remove the solvent. The residue is chromatographed on a column of alumina and eluted with 3% methanol/methylene chloride. The eluate is evaporated to remove the solvent. The residue is washed with ether/isopropyl ether and filtered to give N-(1-ethyl-2-pyrrolidinylmethyl)-2-methoxy-4-methyl-5-dimethylaminosulfonamidobenzamide (211 mg). The product is recrystallized from acetonitrile/isopropyl ether to give crystals melting at 129° to 129.5° C.

Workup

  1. temperatureis refluxed for 39 hours
  2. washThe reaction mixture is washed with aqueous sodium hydrogencarbonate
  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 0.5-1% methanol/methylene chloride
  9. customThe eluate is evaporated

Sources & evidence

ORD record
ord-a3c66e47a0cf4c32adefd6aec1b8e32f
Source dataset
uspto-grants-1982_09
Patent number
US04351770

Reaction notes

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