4-Fluorophenyl isothiocyanate → HCID 86662261, compound

HRID 1627397Notes

Reaction equation

HRID 1627397 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([CH3:17])([CH3:16])[C:12]([NH:14][NH2:15])=[O:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[F:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]=[C:26]=[S:27])=[CH:21][CH:20]=1>CCO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([CH3:17])([CH3:16])[C:12]([NH:14][NH:15][C:26](=[S:27])[NH:25][C:22]2[CH:23]=[CH:24][C:19]([F:18])=[CH:20][CH:21]=2)=[O:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

4

Reactant 2

HCID 152414-Fluorophenyl isothiocyanateHCID 66740370HCID 66740370, compound

Product 1

HCID 86662261HCID 86662261, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-(3,4-dimethoxyphenyl)-2-methylpropanehydrazide (1.04 g, 4.37 mmol) and 4-fluorophenyl isothiocyanate (1.34 g, 8.73 mmol) in EtOH (30 mL) was heated at reflux 2 h. The reaction mixture was cooled and filtered. The filtrate was concentrated in vacuo and the residue was triturated with Et2O. The solids were collected by filtration and dried in vacuo to give 2-(2-(3,4-dimethoxyphenyl)-2-methylpropanoyl)-N-(4-fluorophenyl)hydrazinecarbothioamide (1.23 g, 72%). 1H NMR (400 MHz, DMSO-d6) δ 9.70 (br s, 1H), 9.65 (br s, 1H), 7.38 (b, 1H), 7.17 (t, 3H), 6.94-6.82 (m, 4H), 3.73 (s, 3H), 3.71 (s, 3H), 1.52 (s, 6H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux 2 h
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe residue was triturated with Et2O
  7. filtrationThe solids were collected by filtration
  8. customdried in vacuo

Sources & evidence

ORD record
ord-8e998b9c7b8a4ec2a93796aca0363281
Source dataset
uspto-grants-2014_07
Patent number
US08785488B2

Reaction notes

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