Thionyl Chloride → 2-[2-Amino-4-(1,3-dihydroisoindole-2-carbonyl)quinazolin-6-yl]benzenesulfonyl chloride

HRID 1037685Notes

Reaction equation

[NH2:1][C:2]1[N:11]=[C:10]([C:12]([N:14]2[CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:15]2)=[O:13])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[S:29]([OH:32])(=O)=[O:30])[CH:8]=2)[N:3]=1.S(Cl)([Cl:35])=O>CN(C=O)C>[NH2:1][C:2]1[N:11]=[C:10]([C:12]([N:14]2[CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:15]2)=[O:13])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[S:29]([Cl:35])(=[O:32])=[O:30])[CH:8]=2)[N:3]=1

Participants

Conditions

Temperature: 22 °C

Procedure

40 ml of thionyl chloride together with one drop of DMF are added to a solution of 5 g of 2-[2-amino-4-(1,3-dihydroisoindole-2-carbonyl)quinazolin-6-yl]benzenesulfonic acid. The mixture is stirred at 22° C. for 16 h, evaporated in vacuo, taken up in 500 ml of DCM and extracted twice with 300 ml of water each time. The organic phase is dried over magnesium sulfate, filtered off and evaporated to dryness in vacuo. The residue is employed in the following steps without further purification. Yield: 6.9 g (98%) of 2-[2-amino-4-(1,3-dihydroisoindole-2-carbonyl)quinazolin-6-yl]benzenesulfonyl chloride;

Workup

customevaporated in vacuo
extractionextracted twice with 300 ml of water each time
dry with materialThe organic phase is dried over magnesium sulfate
filtrationfiltered off
customevaporated to dryness in vacuo
customThe residue is employed in the following steps without further purification

Sources & evidence

ORD record: ord-c24e899b52594806b5760e2434585fc2
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546565B2

Reaction notes

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