Benzenesulfonyl chloride → HCID 10501747, compound

HRID 977168Notes

Reaction equation

HRID 977168 reaction equation
[C:1]1([S:7](Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:11][C:12]1[C:21]2[C:16](=[CH:17][C:18]([Cl:22])=[CH:19][CH:20]=2)[NH:15][C:14](=[O:23])[C:13]=1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>>[Cl:22][C:18]1[CH:17]=[C:16]2[C:21]([C:12]([NH:11][S:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)(=[O:9])=[O:8])=[C:13]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:14](=[O:23])[NH:15]2)=[CH:20][CH:19]=1

Participants

3

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 10707207HCID 10707207, compound

Product 1

HCID 10501747HCID 10501747, compound

Procedure

Benzene sulphonylchloride (0.94 ml) and 4-amino-7-chloro-3-phenyl-2(1H)-quinolone (1 g) (Example 2) were reacted in a similar manner to that as described in Example 4. An additional step was required to remove the tert butyldimethylsilyl protecting group using methanolic-HCl for 20 mins to afford the title compound (0.050 g); mp 268° C. (ethanol); δ (360 MHz, DMSO-d6) 7.14 (6H, m, aromatics), 7.32 (5H, m, aromatics), 7.49 (1H, m, aromatics), 7.67 (1H, d, J =8.7 Hz, 5H), 10.02 (1H, br s, 4NH), 12.15 (1H, br s, 1NH); m/z 410 (M+).

Workup

  1. customto remove the tert butyldimethylsilyl protecting group
  2. customfor 20 mins

Sources & evidence

ORD record
ord-47ffd226103347d88e43f86dc0bd468a
Source dataset
uspto-grants-1997_03
Patent number
US05614532

Reaction notes

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