Hydrazine hydrate (1:1) → HCID 22147960, compound

HRID 1823912Notes

Reaction equation

HRID 1823912 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10](=S)[C:11]2[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[CH:14]=[CH:13][C:12]=2F)[CH:6]=[CH:7][CH:8]=1)#[N:2].O.[NH2:23][NH2:24]>C(O)CCC>[N+:17]([C:15]1[CH:16]=[C:11]2[C:12](=[CH:13][CH:14]=1)[NH:24][N:23]=[C:10]2[NH:9][C:5]1[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=1)[C:1]#[N:2])([O-:19])=[O:18]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 22147948HCID 22147948, compound

Product 1

HCID 22147960HCID 22147960, compoundYield 63.1%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

To a solution of N-(3-Cyano-phenyl)-2-fluoro-5-nitro-thiobenzamide (8.56 g; 0.028 mol) in n-butanol (300 mL) was added hydrazine hydrate (2.54 mL; 0.053 mol) and the solution refluxed for 3 hours. The reaction mixture was concentrated in vacuo and triturated with hot ethanol to afford the title compound as a red solid (4.93 g; 62%). 1H NMR (400 MHz, DMSO-d6) δH 7.30 (1H, d), 7.45–7.60 (2H, m), 7.90 (1H, d), 8.20 (1H, d), 8.25 (1H, s), 9.20 (1H, s), 9.85 (1H, s). Mass Spectrum (ES−) m/e=278.28.

Workup

  1. temperaturethe solution refluxed for 3 hours
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customtriturated with hot ethanol

Sources & evidence

ORD record
ord-34c3b495fe9341ef9f062cc35ebcff3b
Source dataset
uspto-grants-2006_05
Patent number
US07041687B2

Reaction notes

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