1-Pyrrolidineethanamine → 4-(7-Chloro-4-quinazolinylamino)-N-[2-(1-pyrrolidinyl)ethyl]benzenesulphonamide

HRID 235654Notes

Reaction equation

HRID 235654 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)=[N:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1.C(=O)([O-])[O-].[Na+].[Na+].[NH2:30][CH2:31][CH2:32][N:33]1[CH2:37][CH2:36][CH2:35][CH2:34]1.C(OCC)(=O)C>O.C(Cl)(Cl)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]([NH:30][CH2:31][CH2:32][N:33]4[CH2:37][CH2:36][CH2:35][CH2:34]4)(=[O:22])=[O:21])=[CH:16][CH:15]=3)=[N:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 13441-PyrrolidineethanamineHCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 212739544-(7-Chloro-4-quinazolinylamino)benzenesulphonyl chloride hydrochloride

Product 1

HCID 135372054-(7-Chloro-4-quinazolinylamino)-N-[2-(1-pyrrolidinyl)ethyl]benzenesulphonamideYield 26.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

4-(7-Chloro-4-quinazolinylamino)benzene sulphonyl chloride, hydrochloride (3.5 g, 0.011 mole) was added portionwise to a well-stirred mixture of sodium carbonate (11.5 g) in water (120 ml) and N-(2-aminoethyl)-pyrrolidine (1.26 g, 0.01 mole) in chloroform (120 ml) at about 10° C. After 1 hour at room temperature, the mixture was filtered. The chloroform layer was separated, dried (MgSO4) and evaporated under reduced pressure to give a gum. Trituration from ethyl acetate gave a white solid (1.14 g) which could be crystallised from ethanol-water, m.p. 203°-204.5° C.

Workup

  1. filtrationthe mixture was filtered
  2. customThe chloroform layer was separated
  3. dry with materialdried (MgSO4)
  4. customevaporated under reduced pressure
  5. customto give a gum

Sources & evidence

ORD record
ord-577062e55a6e44218a7f8aacbe34dcc6
Source dataset
uspto-grants-1987_02
Patent number
US04640920

Reaction notes

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