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

HRID 840916Notes

Reaction equation

HRID 840916 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:18]=[C:19]([NH:23][NH2:24])[CH:20]=[CH:21][CH:22]=1>C(O)C>[F:16][C:17]1[CH:18]=[C:19]([NH:23][N:24]=[C:10]2[C:11]3[C:7](=[CH:6][CH:5]=[C:4]4[N:3]=[CH:2][S:1][C:12]4=3)[NH:8][C:9]2=[O:14])[CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 27239143-Fluorophenylhydrazine hydrochlorideHCID 117457566H-thiazolo[5,4-e]indole-7,8-dione

Product 1

HCID 1785170078-[2-(3-fluorophenyl)hydrazinyl]pyrrolo[2,3-g][1,3]benzothiazol-7-oneYield 60.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

6H-1-Thia-3,6-diaza-as-indacen-7,8-dione (Procedure A, 50 mg, 0.25 mmol) was combined with 3-fluorophenylhydrazine hydrochloride (50 mg, 0.3 mmol) in 2 ml of ethanol and heated at 70° C. for 6 hrs. The product was collected by filtration of the hot solution, washing with ethanol and diethyl ether, to give 47 mg (60%) of the title compound as a brown solid. 1H NMR (DMSO-d6): δ6.82 (t, J=8.7 Hz, 1H); 7.10 (d, J=8.6 Hz, 1H); 7.37 (m, 2H); 7.41 (dd, 1H); 7.97 (d, J=8.6 Hz, 1H); 9.25 (s, 1H); 11.2 (s, 1H). ES−MS m/z 311 (M−1)−.

Workup

  1. filtrationThe product was collected by filtration of the hot solution
  2. washwashing with ethanol and diethyl ether

Sources & evidence

ORD record
ord-60413d6fa20643df910b8a4b148512fe
Source dataset
uspto-grants-2002_04
Patent number
US06369086B1

Reaction notes

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