4-Fluorophenylhydrazine hydrochloride → 8-[2-(4-fluorophenyl)hydrazinyl]pyrrolo[2,3-g][1,3]benzothiazol-7-one

HRID 840917Notes

Reaction equation

HRID 840917 reaction equation
[S:1]1[C:12]2[C:4](=[CH:5][CH:6]=[C:7]3[C:11]=2[C:10](=O)[C:9](=[O:14])[NH:8]3)[N:3]=[CH:2]1.Cl.[F:16][C:17]1[CH:22]=[CH:21][C:20]([NH:23][NH2:24])=[CH:19][CH:18]=1>>[F:16][C:17]1[CH:22]=[CH:21][C:20]([NH:23]/[N:24]=[C:10]2\[C:9](=[O:14])[NH:8][C:7]3[C:11]\2=[C:12]2[S:1][CH:2]=[N:3][C:4]2=[CH:5][CH:6]=3)=[CH:19][CH:18]=1

Participants

3

Reactant 2

HCID 699814-Fluorophenylhydrazine hydrochlorideHCID 117457566H-thiazolo[5,4-e]indole-7,8-dione

Product 1

HCID 1785170088-[2-(4-fluorophenyl)hydrazinyl]pyrrolo[2,3-g][1,3]benzothiazol-7-oneYield 49%

Procedure

Prepared according to Example 96 with 6H-1-thia-3,6-diaza-as-indacen-7,8-dione (Procedure A) and 4-fluorophenylhydrazine hydrochloride in 49% yield. 1H NMR (DMSO-d6): δ7.11 (d, J=8.6 Hz, 1H); 7.25 (t, J=8.8 Hz, 2H); 7.52 (dd, J=4.8, 8.8 Hz, 2H); 7.94 (d, J=8.6 Hz, 1H); 9.27 (s, 1H); 11.2 (s, 1H); 12.6 (s, 1H). ES−MS m/z 311 (M−1)−.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-3b931100663843ddae5f99487c70fd55
Source dataset
uspto-grants-2002_04
Patent number
US06369086B1

Reaction notes

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