Sodium Carbonate → 4-(7-Trifluoromethyl-4-quinolinylamino)-N-[(1-ethyl-2-pyrrolidinyl) methyl]benzenesulphonamide

HRID 2309374Notes

Reaction equation

HRID 2309374 reaction equation
Cl.[F:2][C:3]([F:26])([F:25])[C:4]1[CH:13]=[C:12]2[C:7]([C:8]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=3)=[CH:9][CH:10]=[N:11]2)=[CH:6][CH:5]=1.C(=O)([O-])[O-].[Na+].[Na+].[NH2:33][CH2:34][CH:35]1[CH2:39][CH2:38][CH2:37][N:36]1[CH2:40][CH3:41]>C(Cl)(Cl)Cl>[F:2][C:3]([F:26])([F:25])[C:4]1[CH:13]=[C:12]2[C:7]([C:8]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([S:21]([NH:33][CH2:34][CH:35]4[CH2:39][CH2:38][CH2:37][N:36]4[CH2:40][CH3:41])(=[O:23])=[O:22])=[CH:17][CH:16]=3)=[CH:9][CH:10]=[N:11]2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 1172952-Aminomethyl-1-ethylpyrrolidineHCID 201495894-(7-Trifluoromethyl-4-quinolinylamino)benzenesulphonyl chloride hydrochloride

Product 1

HCID 137471374-(7-Trifluoromethyl-4-quinolinylamino)-N-[(1-ethyl-2-pyrrolidinyl) methyl]benzenesulphonamideYield 28.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

4-(7-Trifluoromethyl-4-quinolinylamino)benzenesulphonyl chloride hydrochloride (4.3 g, 0.01 mol) was added portionwise to a well stirred mixture of aqueous sodium carbonate (12.3 g in 70 ml of water) and 2-aminomethyl-1-ethylpyrrolidine (1.3 g, 0.01 mol) in chloroform (70 ml) at about 10° C. The ice bath used for cooling was removed and, after 11/2 hours, the mixture was filtered. The solid was washed with water and then air-dried. Recrystallisation from ethanol-water, followed by drying, gave the title compound (1.35 g), melting point 194°-5° C.

Workup

  1. temperaturefor cooling
  2. customwas removed
  3. filtrationafter 11/2 hours, the mixture was filtered
  4. washThe solid was washed with water
  5. customair-dried
  6. customRecrystallisation from ethanol-water
  7. customby drying

Sources & evidence

ORD record
ord-f1c93a06b55d4553b30adbc7f5a4e57a
Source dataset
uspto-grants-1987_09
Patent number
US04695574

Reaction notes

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