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

HRID 1884010Notes

Reaction equation

[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

Participants

Reactant 2

HCID 24638Chlorosulfonic acid

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

Product 1

HCID 1361209353-Amino-8-bromo-5,6-dihydrobenzo[f]quinazolin-1(2h)-one-9-sulfonylchlorideYield 104.3%

Procedure

Chlorosulfonic acid (100 g) was added to 3-amino-8-bromo-5,6-dihydro-benzo[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, ArCH2), 2.81-2.88 (m, 2H, ArCH2), 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 C12H9BrClN3O3S1/2H2O.9/20H2SO4: 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.

Workup

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

Sources & evidence

ORD record: ord-98fcc0ca5f3f4208997e41ecc811a5c1
Source dataset: uspto-grants-2004_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06762188B1

Reaction notes

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