Hydrochloric Acid → 1-[4-(7-Chloro-4-quinazolinylamino)benzenesulphonyl]-4-methylpiperazine

HRID 570053Notes

Reaction equation

[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.C(=O)([O-])[O-].[Na+].[Na+].Cl.[Cl:15][C:16]1[CH:25]=[C:24]2[C:19]([C:20]([NH:26][C:27]3[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=3)=[N:21][CH:22]=[N:23]2)=[CH:18][CH:17]=1.Cl>C(Cl)(Cl)Cl.O.C(O)C>[Cl:15][C:16]1[CH:25]=[C:24]2[C:19]([C:20]([NH:26][C:27]3[CH:28]=[CH:29][C:30]([S:33]([N:5]4[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]4)(=[O:34])=[O:35])=[CH:31][CH:32]=3)=[N:21][CH:22]=[N:23]2)=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 10 °C

Procedure

N-Methylpiperazine (1.0 g, 0.01 mole) was dissolved in chloroform (50 ml). Sodium carbonate (10 g) was dissolved in water (50 ml). The solutions were combined and cooled to 10° C. 4-(7-Chloro-4-quinazolinylamino)benzenesulphonyl chloride hydrochloride (3.85 g, 0.01 mole) was added in portions to the vigorously stirred solution. Stirring was continued for one hour. The chloroform layer was separated, dried and evaporated. The resulting gummy solid was redissolved in chloroform and chromatographed on an alumina column. Elution with chloroform gave a first band which was discarded. The second band was obtained as a low melting solid, which was converted to the hydrochloride by dissolving in ethanol and adding ethereal hydrogen chloride to give the title compound as the sesquihydrochloride (650 mg) m.p. 237°-239° C.

Workup

customThe chloroform layer was separated
customdried
customevaporated
dissolutionThe resulting gummy solid was redissolved in chloroform
customchromatographed on an alumina column
washElution with chloroform
customgave a first band which
customThe second band was obtained as a low melting solid, which

Sources & evidence

ORD record: ord-067f969d2e5d4976854d945aa56161e4
Source dataset: uspto-grants-1988_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04734510

Reaction notes

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