3-(Trifluoromethyl)phenylcyanamide → HCID 178490592, compound

HRID 636684

Reaction equation

HRID 636684 reaction equation
[NH:1]([C:4]1[CH:5]=[C:6]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:8][CH:9]=1)[C:2]#[N:3].Cl.[CH3:15][O:16][C:17]1[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][C:18]=1[NH2:19]>C(#N)C>[CH3:15][O:16][C:17]1[CH:23]=[CH:22][C:21]([C:24]([F:25])([F:26])[F:27])=[CH:20][C:18]=1[NH:19][C:2]([NH:1][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:11])([F:12])[F:13])[CH:5]=1)=[NH:3]

Participants

4

Reactant 2

HCID 110741023-(Trifluoromethyl)phenylcyanamideHCID 700096092-Methoxy-5-(trifluoromethyl)aniline hydrochloride

Product 1

HCID 178490592HCID 178490592, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3-cyanamidobenzotrifluoride (0.40 g, 2.15 mmol), 2-methoxy-5-triflouromethylaniline hydrochloric acid salt (0.53 g, 2.33 mmol) and acetonitrile (20 ml) was stirred at reflux for 40 h. The solvent was evaporated. Dichloromethane (50 ml) was added and the mixture was washed with saturated aqueous sodium hydrogen carbonate (50 ml). The organic phase was purified by chromatography using silica gel and a mixture of methanol (10%) and dichloromethane as eluent. The product was isolated as the free base. Yield 0.40 g, 49%. M.p. 45-47° C.

Workup

  1. temperatureat reflux for 40 h
  2. customThe solvent was evaporated
  3. additionDichloromethane (50 ml) was added
  4. washthe mixture was washed with saturated aqueous sodium hydrogen carbonate (50 ml)
  5. customThe organic phase was purified by chromatography
  6. additiona mixture of methanol (10%) and dichloromethane as eluent
  7. customThe product was isolated as the free base

Sources & evidence

ORD record
ord-8d904f464e7541fe803fbfa70b6cc7c7
Source dataset
uspto-grants-2001_02
Patent number
US06194447B1

Linked notes

Loading…