Triethylamine → N-[4-[2-(Dimethylamino)ethoxy]benzyl]-5-dimethylaminosulfonyl 2-methoxybenzamide

HRID 703532Notes

Reaction equation

HRID 703532 reaction equation
[CH3:1][N:2]([CH3:17])[S:3]([C:6]1[CH:7]=[CH:8][C:9]([O:15][CH3:16])=[C:10]([CH:14]=1)[C:11]([OH:13])=O)(=[O:5])=[O:4].C(N(CC)CC)C.ClC(OCC)=O.[CH3:31][N:32]([CH3:44])[CH2:33][CH2:34][O:35][C:36]1[CH:43]=[CH:42][C:39]([CH2:40][NH2:41])=[CH:38][CH:37]=1>O1CCCC1>[CH3:31][N:32]([CH3:44])[CH2:33][CH2:34][O:35][C:36]1[CH:43]=[CH:42][C:39]([CH2:40][NH:41][C:11](=[O:13])[C:10]2[CH:14]=[C:6]([S:3]([N:2]([CH3:1])[CH3:17])(=[O:4])=[O:5])[CH:7]=[CH:8][C:9]=2[O:15][CH3:16])=[CH:38][CH:37]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 88349p-(2-(Dimethylamino)ethoxy)benzylamineHCID 135768955-(N,N-dimethylsulfamoyl)-2-methoxybenzoic acid

Product 1

HCID 15622788N-[4-[2-(Dimethylamino)ethoxy]benzyl]-5-dimethylaminosulfonyl 2-methoxybenzamideYield 91.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a cooled suspension of 3.20 g of 5-dimethylaminosulfonyl-2-methoxybenzoic acid in 10 ml of tetrahydrofuran were successively added dropwise 1.25 g of triethylamine and 1.34 g of ethyl chloroformate with stirring. The mixture was stirred at the same temperature for 30 minutes and then a solution of 2.00 g of 4-[2-(dimethylamino)ethoxy]benzylamine in 10 ml of tetrahydrofuran was added dropwise with stirring. The mixture was stirred at room temperature for 2 hours and the solvent was evaporated. Hydrochloric acid (10%) was added to the residue and the aqueous solution was washed with ethyl acetate. The aqueous layer was made alkaline with potassium carbonate and was extracted with ethyl acetate. The extract was dried and evaporated. The residue was washed with isopropyl ether to give 4.10 g of colorless crystals, which were recrystallized from a mixture of ethyl acetate and ether to give colorless needles, m.p. 99.5°-100.5° C.

Workup

  1. stirringThe mixture was stirred at the same temperature for 30 minutes
  2. stirringwith stirring
  3. stirringThe mixture was stirred at room temperature for 2 hours
  4. customthe solvent was evaporated
  5. additionHydrochloric acid (10%) was added to the residue
  6. washthe aqueous solution was washed with ethyl acetate
  7. extractionwas extracted with ethyl acetate
  8. customThe extract was dried
  9. customevaporated
  10. washThe residue was washed with isopropyl ether

Sources & evidence

ORD record
ord-0998027b0f7c46eb9408bc62bd472629
Source dataset
uspto-grants-1991_01
Patent number
US04983633

Reaction notes

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