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

HRID 2309375Notes

Reaction equation

HRID 2309375 reaction equation
Cl.[Cl:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=3)=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1.C(=O)([O-])[O-].[Na+].[Na+].[NH2:30][CH2:31][CH:32]1[CH2:36][CH2:35][CH2:34][N:33]1[CH2:37][CH2:38][CH3:39]>C(Cl)(Cl)Cl.O>[Cl:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([S:20]([NH:30][CH2:31][CH:32]4[CH2:36][CH2:35][CH2:34][N:33]4[CH2:37][CH2:38][CH3:39])(=[O:22])=[O:21])=[CH:16][CH:15]=3)=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 12829004(1-Propylpyrrolidin-2-YL)methanamineHCID 201495884-(7-Chloro-4-quinolinylamino)benzenesulphonyl chloride hydrochloride

Product 1

HCID 137471394-(7-Chloro-4-quinolinylamino)-N-[(1-propyl-2-pyrrolidinyl) methyl]benzenesulphonamideYield 28%

Reagents, catalysts & solvents 1

HCID 22418719Chloroform waterSolvent

Procedure

4-(7-Chloro-4-quinolinylamino)benzenesulphonyl chloride hydrochloride (5.4 g, 0.014 mol) was added portionwise to a well-stirred two phase mixture of chloroform/water (140 ml/140 ml) containing sodium carbonate (14.8 g) and 2-aminomethyl-1-propylpyrrolidine (2.0 g, 0.014 mol) at about 10° C. The mixture was allowed to warm to room temperature, then stirred for 11/2 hours. The chloroform layer was separated, dried (MgSO4) and evaporated under reduced pressure to give a gum. The gum was crystallised from ethanol/water to give a pale yellow solid (1.8 g). A further recrystallisation from ethanol gave the title compound (0.5 g), melting point 192.5°-194° C.

Workup

  1. stirringstirred for 11/2 hours
  2. customThe chloroform layer was separated
  3. dry with materialdried (MgSO4)
  4. customevaporated under reduced pressure
  5. customto give a gum
  6. customThe gum was crystallised from ethanol/water

Sources & evidence

ORD record
ord-806c9295ba9741f4acdff4851f0a4b9b
Source dataset
uspto-grants-1987_09
Patent number
US04695574

Reaction notes

Loading…