4-Amino-2,6-dimethylphenol → HCID 21906981, compound

HRID 840895Notes

Reaction equation

HRID 840895 reaction equation
OC1C(C)=CC(N)=CC=1C.[OH:11][C:12]1[C:13]([CH3:24])=[C:14]2[C:18](=[CH:19][C:20]=1[CH3:21])[NH:17][C:16](=[O:22])[C:15]2=[O:23].[CH:25]1[C:30]([NH:31][NH2:32])=[CH:29][CH:28]=[C:27]([S:33]([NH2:36])(=[O:35])=[O:34])[CH:26]=1.Cl>O>[OH:11][C:12]1[C:13]([CH3:24])=[C:14]2[C:18](=[CH:19][C:20]=1[CH3:21])[NH:17][C:16](=[O:22])[C:15]2=[O:23].[OH:11][C:12]1[C:13]([CH3:24])=[C:14]2[C:18](=[CH:19][C:20]=1[CH3:21])[NH:17][C:16](=[O:22])[C:15]2=[N:32][NH:31][C:30]1[CH:29]=[CH:28][C:27]([S:33]([NH2:36])(=[O:34])=[O:35])=[CH:26][CH:25]=1

Participants

6

Reactant 3

HCID 826684-Amino-2,6-dimethylphenolHCID 27945674-Hydrazinylbenzenesulfonamide hydrochlorideHCID 21906981HCID 21906981, compound

Product 2

HCID 21906981HCID 21906981, compoundHCID 178421878HCID 178421878, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5-Hydroxy-4,6-dimethyl-1H-indole-2,3-dione was prepared from 4-hydroxy-3,5-dimethylaniline according to Procedure A. The title compound was prepared from 5-hydroxy-4,6-dimethyl-1H-indole-2,3-dione and 4-sulfonamidophenylhydrazine hydrochloride according to Procedure G: mp>250° C.; 1H NMR (DMSO-d6): δ2.18 (s, 3H), 2.47 (s, 3H), 6.50 (s, 1H), 7.22 (s, 2H), 7.44 (d, J=8.7 Hz, 2H), 7.77 (d, J=8.7 Hz, 2H), 7.99 (s, 1H), 10.78(s, 1H), 12.98 (s,1H); APCI−MS: m/z 359 (M−H)−. Anal. Calcd for C16H16N4O4S.0.25 H2O: C, 52.67; H, 4.56; N, 15.35; S, 8.79. Found: C, 52.69; H, 4.47; N, 15.33; S, 8.87.

Sources & evidence

ORD record
ord-d1e346cbca7241eb92b09f14376ab779
Source dataset
uspto-grants-2002_04
Patent number
US06369086B1

Reaction notes

Loading…