Triethylamine → Benzamide, 5-(aminosulfonyl)-N-((4-(2-(dimethylamino)ethoxy)phenyl)methyl)-2-methoxy-

HRID 703531Notes

Reaction equation

HRID 703531 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:9]([S:12](=[O:15])(=[O:14])[NH2:13])=[CH:8][C:4]=1[C:5]([OH:7])=O.C(N(CC)CC)C.C(Cl)(=O)C(C)(C)C.[CH3:30][N:31]([CH3:43])[CH2:32][CH2:33][O:34][C:35]1[CH:42]=[CH:41][C:38]([CH2:39][NH2:40])=[CH:37][CH:36]=1>O1CCCC1>[CH3:30][N:31]([CH3:43])[CH2:32][CH2:33][O:34][C:35]1[CH:42]=[CH:41][C:38]([CH2:39][NH:40][C:5](=[O:7])[C:4]2[CH:8]=[C:9]([S:12](=[O:15])(=[O:14])[NH2:13])[CH:10]=[CH:11][C:3]=2[O:2][CH3:1])=[CH:37][CH:36]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 88349p-(2-(Dimethylamino)ethoxy)benzylamineHCID 896012-Methoxy-5-sulfamoylbenzoic acid

Product 1

HCID 3078818Benzamide, 5-(aminosulfonyl)-N-((4-(2-(dimethylamino)ethoxy)phenyl)methyl)-2-methoxy-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a cooled suspension of 14.3 g of 2-methoxy-5-sulfamoylbenzoic acid in 60 ml of tetrahydrofuran were successively added dropwise 6.25 g of triethylamine and 7.45 g of pivaloyl chloride with stirring. The mixture was stirred at the same temperature for 1 hour and then a solution of 10.0 g of 4-[2-(dimethylamino)ethoxy]-benzylamine in 40 ml of tetrahydrofuran was added dropwise with stirring. The mixture was stirred at room temperature for 14 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 to give a precipitate, which was washed with water and ethyl acetate, of 16.6 g of colorless crystals. Recrystallization of the crystals from ethanol gave the title compound as colorless needles, m.p. 154°-155° C.

Workup

  1. stirringThe mixture was stirred at the same temperature for 1 hour
  2. stirringwith stirring
  3. stirringThe mixture was stirred at room temperature for 14 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. customto give a precipitate, which
  8. washwas washed with water and ethyl acetate, of 16.6 g of colorless crystals
  9. customRecrystallization of the crystals from ethanol

Sources & evidence

ORD record
ord-eb8374643ebd448ba29a3b71e5fb0c69
Source dataset
uspto-grants-1991_01
Patent number
US04983633

Reaction notes

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