[2,6-Dichloro-4-(trifluoromethyl)phenyl]hydrazine → HCID 18668830, compound

HRID 1058569Notes

Reaction equation

HRID 1058569 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[NH:13][NH2:14].[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][S:24][C:25](=[C:36]([C:39]#[N:40])[C:37]#[N:38])SCC2C=CC(OC)=CC=2)=[CH:19][CH:18]=1>C(O)(C)C>[NH2:40][C:39]1[N:13]([C:3]2[C:2]([Cl:1])=[CH:7][C:6]([C:8]([F:9])([F:11])[F:10])=[CH:5][C:4]=2[Cl:12])[N:14]=[C:25]([S:24][CH2:23][C:20]2[CH:19]=[CH:18][C:17]([O:16][CH3:15])=[CH:22][CH:21]=2)[C:36]=1[C:37]#[N:38]

Participants

4

Reactant 2

HCID 688223[2,6-Dichloro-4-(trifluoromethyl)phenyl]hydrazineHCID 18668831HCID 18668831, compound

Product 1

HCID 18668830HCID 18668830, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 2,6-dichloro-4-trifluoromethyl phenyl hydrazine (245 mg, 1.0 mmol) and {bis[(4-methoxyphenyl)methylthio]methylene}methane-1,1-dicarbonitrile (101, 382 mg, 1.0 mmol) in isopropyl alcohol (15 mL) was heated at reflux for 16 h. The solvent was removed under reduced pressure and the desired product 102 obtained after chromatographic separation (silica gel) using ethyl acetate-hexanes (331 mg, 70%). NMR (δ, CDCl3): 7.7 (2H, s); 7.2 (2H, d, J=8.7 Hz); 6.8 (2H, d, J=8.7 Hz); 4.41 (2H, broad); 4.23 (2H, s). MS: M+1=473 (calc.: 473).

Workup

  1. temperatureat reflux for 16 h
  2. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-e7415f1bb8ea4abc8cf196c98e7a2e99
Source dataset
uspto-grants-2003_02
Patent number
US06518266B1

Reaction notes

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