Chlorosulfonic acid → 3-Amino-8-bromo-5,6-dihydrobenzo[f]quinazolin-1(2h)-one-9-sulfonylchloride

HRID 1654362

Reaktionsgleichung

Reaktionsgleichung von HRID 1654362
[Cl:1][S:2]([OH:5])(=O)=[O:3].[NH2:6][C:7]1[NH:16][C:15](=[O:17])[C:14]2[C:13]3[CH:18]=[CH:19][C:20]([Br:22])=[CH:21][C:12]=3[CH2:11][CH2:10][C:9]=2[N:8]=1>>[NH2:6][C:7]1[NH:16][C:15](=[O:17])[C:14]2[C:13]3[CH:18]=[C:19]([S:2]([Cl:1])(=[O:5])=[O:3])[C:20]([Br:22])=[CH:21][C:12]=3[CH2:11][CH2:10][C:9]=2[N:8]=1

Komponenten

3

Edukt 2

HCID 24638Chlorosulfonic acidHCID 1358381833-amino-8-bromo-5,6-dihydrobenzo[f]quinazolin-1(2H)-one

Produkt 1

HCID 1361209353-Amino-8-bromo-5,6-dihydrobenzo[f]quinazolin-1(2h)-one-9-sulfonylchlorideAusbeute 104,3 %

Versuchsvorschrift

Chlorosulfonic acid(100 g) was added to 3-amino-8-bromo-5,6-dihydrobenzo[f] quinazolin-1(2H)-one(5.20 g,17.8 mmole) and the solution stirred overnight at room temperature. The reaction mixture was poured over ice, the collected solid washed with water, and dried under high vacuum to give 3-amino-8-bromo-5,6-dihydrobenzo[f]quinazolin-1(2H)-one-9-sulfonyl chloride(7.25 g,90%). 1H NMR (DMSO-d6, 200 MHz) δ: 2.67-2.75 (m, 2H, Ar CH2), 2.81-2.88 (m, 2H, Ar CH2), 7.43 (s, 1H, Ar), 8.23 (br s, 2H, NH2), 8.91(s, 1H, Ar), 9.90-10.50 (v br s, 1H, NH). Anal Calculated for C12H9BrClN3O3S 1/2 H2O.9/20 H2SO4 : C,32.48; H,2.48; N,9.47; S,10.46. Found: C,32.68; H,2.37; N,9.20; S,10.40.

Aufarbeitung

  1. additionThe reaction mixture was poured over ice
  2. washthe collected solid washed with water
  3. customdried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-5624e31c3a734c119a083a3d22407b6e
Quelldatensatz
uspto-grants-1995_04
Patentnummer
US05405851

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