Phenol, 4-amino-2-(1-methylethyl)- (9CI) → HCID 21956235, compound

HRID 840889Notes

Reaction equation

HRID 840889 reaction equation
C(C1C=C(C=CC=1O)N)(C)C.[OH:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][C:21]=1[CH:22]([CH3:24])[CH3:23])[NH:18][C:17](=[O:25])[C:16]2=[O:26].[CH:27]1[C:32]([NH:33][NH2:34])=[CH:31][CH:30]=[C:29]([S:35]([NH2:38])(=[O:37])=[O:36])[CH:28]=1.Cl>>[OH:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][C:21]=1[CH:22]([CH3:24])[CH3:23])[NH:18][C:17](=[O:25])[C:16]2=[O:26].[OH:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][C:21]=1[CH:22]([CH3:24])[CH3:23])[NH:18][C:17](=[O:25])[C:16]2=[N:34][NH:33][C:32]1[CH:31]=[CH:30][C:29]([S:35]([NH2:38])(=[O:36])=[O:37])=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 586009Phenol, 4-amino-2-(1-methylethyl)- (9CI)HCID 27945674-Hydrazinylbenzenesulfonamide hydrochlorideHCID 21956235HCID 21956235, compound

Product 2

HCID 21956235HCID 21956235, compoundHCID 178438363HCID 178438363, compound

Procedure

5-Hydroxy-6-isopropyl-1H-indole-2,3-dione was prepared from 3-isopropyl-4-hydroxyaniline according to Procedure A: 1H NMR (DMSO-d6): δ1.12 (d, J=6.8 Hz, 6H), 3.21 (septet, J=6.9 Hz, 1H), 6.62 (s, 1H), 6.82 (s,1H), 9.51 (1H), 10.61 (s, 1H); ESI−MS m/z 204 (M−H)−. The title compound was prepared from 5-hydroxy-6-isopropyl-1H-indole-2,3-dione and 4-sulfonamidophenylhydrazine hydrochloride according to Procedure G: mp>250° C.; 1H NMR (DMSO-d6): δ1.12 (d, J=7.0 Hz, 6H), 3.21 (septet, J=6.8 Hz, 1H), 6.62 (s, 1H), 6.97 (s, 1H), 7.21 (s, 2H), 7.45 (d, J=8.9 Hz, 2H), 7.75 (d, J=8.7 Hz, 2H), 9.11 (s, 1H), 10.70 (s, 1H), 12.74 (s, 1H); ESI−MS m/z 373 (M−H)−. Anal. Calcd for C17H18N4O4S: C, 54.53; H, 4.85; N, 14.96; S, 8.56. Found: C, 54.37; H, 4.95; N, 14.84; S, 8.48.

Sources & evidence

ORD record
ord-af5d263031f14a39b0605e86efb8aaab
Source dataset
uspto-grants-2002_04
Patent number
US06369086B1

Reaction notes

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