HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-Methyl-1,3-benzoxazol-6-amine → N-(6-hydroxy-2,3-dioxo-2,3-dihydro-1H-indol-4-yl)acetamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2-Methyl-1,3-benzoxazol-6-amine | HCID 590539 | — |
| Reactant | 4-Hydrazinylbenzenesulfonamide hydrochloride | HCID 2794567 | — |
| Reactant | N-(6-hydroxy-2,3-dioxo-2,3-dihydro-1H-indol-4-yl)acetamide | HCID 21956268 | — |
| Product | N-(6-hydroxy-2,3-dioxo-2,3-dihydro-1H-indol-4-yl)acetamide | HCID 21956268 | — |
| Product | 4-[2-(2-methyl-6-oxopyrrolo[3,2-f][1,3]benzoxazol-7-yl)hydrazinyl]benzenesulfonamide | HCID 178432044 | — |
Reaction Steps
N-(6-Hydroxy-2,3-dioxo-2,3-dihydro-1H-indol-4-yl)acetamide was prepared from 6-amino-2-methylbenzoxazole (Heleyova, et al., Collection of Czechoslovakian Chemical Communications 1996, 61, 371-80) according to Procedure A in 12% overall yield. Condensation of N-(6-hydroxy-2,3-dioxo-2,3-dihydro-1H-indol-4-yl)acetamide and 4-sulfonamidophenylhydrazine hydrochloride according to Procedure G gave the title compound in 6% yield: 1H NMR (DMSO-d6): δ 2.55 (s, 3H), 7.13 (s, 1H), 7.23 (s, 2H), 7.57 (d, J=8.8 Hz, 2H), 7.76 (d, J=8.8 Hz, 2H), 7.78 (s, 1H), 11.12 (s, 1H), 12.67 (s, 1H); APCI−MS m/z 370 (M−H)−. Anal. Calcd for C16H15N5O4S: C, 51.75, H, 3.53; N, 18.86; S, 8.86. Found C, 51.50, H, 3.61; N, 18.69; S. 8.49.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06387919B1 |
| Source dataset | uspto-grants-2002_05 |
| ORD ID | ord-ef553b0653b64895a4fbe4a36fa716f9 |
| Source note | uspto-grants-2002_05 |