P-Toluenesulfonamide → HCID 10270136, compound

HRID 2086007Notes

Reaction equation

HRID 2086007 reaction equation
[NH2:1][C:2]1[CH:15]=[CH:14][C:13]2[NH:12][C:11](=[O:16])[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[C:4]=2[CH:3]=1.[CH3:17][C:18]1[CH:23]=[CH:22][C:21]([S:24](N)(=[O:26])=[O:25])=[CH:20][CH:19]=1>C1OCCOC1>[O:16]=[C:11]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]2[CH:3]=[C:2]([NH:1][S:24]([C:21]3[CH:22]=[CH:23][C:18]([CH3:17])=[CH:19][CH:20]=3)(=[O:26])=[O:25])[CH:15]=[CH:14][C:13]=2[NH:12]1

Participants

4

Reactant 2

HCID 6269P-ToluenesulfonamideHCID 2706686(5h)-Phenanthridinone, 2-amino-

Product 1

HCID 10270136HCID 10270136, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Prepared from 2-amino-6(5H)-phenanthridinone 3 and 4-methyl benzenesulfonamide according to General Procedure A. P-dioxane was used as solvent and the reaction was run at 40° C. for 30 hours. Purification of compound by crystallization in dioxane gave a brown solid (93% yield). mp 199-203° C. 1H-NMR (400 MHz, DMSO-d6), 10.20 (s, 1H), 8.30 (d, J=8.0 Hz, 1H), 8.15 (d, J=8.1 Hz, 1H), 7.95 (s, 1H), 7.88 (t, J=7.6, 1H), 7.65 (m, 3H), 7.33 (d, J=8.2 Hz, 2H), 7.19 (m, 2H). Anal. (C20H16N2O3S), C H N.

Workup

  1. customPurification of compound
  2. customby crystallization in dioxane

Sources & evidence

ORD record
ord-762ed160bbb541b29ddc2b9c4bedecfd
Source dataset
uspto-grants-2004_04
Patent number
US06723733B2

Reaction notes

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