Dichloromethane → 4-(7-Chloro-4-quinazolinylamino)-N-(2-diethylaminoethyl) benzenesulphonamide

HRID 235650Notes

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.Cl.S(Cl)(Cl)(=O)=O.C(Cl)Cl.[CH2:33]([N:35]([CH2:39][CH3:40])[CH2:36][CH2:37][NH2:38])[CH3:34]>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:38][CH2:37][CH2:36][N:35]([CH2:39][CH3:40])[CH2:33][CH3:34])(=[O:22])=[O:21])=[CH:16][CH:15]=3)=[N:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 10 °C

Procedure

4-(7-Chloro-4-quinazolinylamino)benzenesulphonyl chloride hydrochloride (36.0 g obtainable from the title compound of Example 1) and methylene chloride (180 ml) were cooled under nitrogen to 5° C. N,N-Diethylethylenediamine (35.4 g) was then added at 5°-10° C. over 20 minutes to give a light yellow solution. The solution was stirred for 2 hours under nitrogen at 5° to 15° C. and then water (200 ml) was added. A white solid precipitated. The mixture was cooled to 10° C. and the solid was filtered off, washed with water (2×40 ml) and with chloroform (2×40 ml) and dried in an oven to give 279 g of title compound.

Workup

customto give a light yellow solution
customA white solid precipitated
filtrationthe solid was filtered off
washwashed with water (2×40 ml) and with chloroform (2×40 ml)
customdried in an oven

Sources & evidence

ORD record: ord-8665aaec3b5e4843bf2169866c7a0ac4
Source dataset: uspto-grants-1987_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04640920

Reaction notes

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