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

HRID 1383067Notes

Reaction equation

[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[Na].Cl.[Cl:10][C:11]1[CH:20]=[C:19]2[C:14]([C:15]([NH:21][C:22]3[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=3)=[N:16][CH:17]=[N:18]2)=[CH:13][CH:12]=1.Cl>C(Cl)(Cl)Cl.O.C(O)C>[Cl:10][C:11]1[CH:20]=[C:19]2[C:14]([C:15]([NH:21][C:22]3[CH:23]=[CH:24][C:25]([S:28]([N:5]4[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]4)(=[O:29])=[O:30])=[CH:26][CH:27]=3)=[N:16][CH:17]=[N:18]2)=[CH:13][CH:12]=1

Participants

Conditions

Temperature: 10 °C

Procedure

N-Methylpiperazine (1.0 g, 0.01 mole) was dissolved in chloroform (50 ml). Sodium carbonte (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-66952805a21a4dbf86c009a48c9b825b
Source dataset: uspto-grants-1989_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04808715

Reaction notes

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