Toluene → HCID 70019311, compound

HRID 1358160Notes

Reaction equation

HRID 1358160 reaction equation
CC1C=CC([CH:6]=[S:7])=CC=1.[CH3:10][N:11]([CH3:13])[NH2:12].[C:14]1([CH3:20])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>[Cl-].[Na+].O.CC(C)=O.CCCCCC>[CH3:10][N:11]([CH3:13])[N:12]=[CH:20][C:14]1[CH:19]=[CH:18][C:17]([S:7][CH3:6])=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 1140TolueneHCID 59761,1-DimethylhydrazineHCID 181775354-Methylthiobenzaldehyde

Product 1

HCID 70019311HCID 70019311, compound

Reagents, catalysts & solvents 2

HCID 21880519Acetone hexaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

7.44 g (48.9 mmol) of 4-methylthiobenzaldehyde and 4.0 ml (52.7 mmol) of 1,1-dimethylhydrazine are dissolved in toluene (50 ml) and heated to reflux for 2.5 hr. Brine is added to the reaction mixture after cooling, and the product is extracted with toluene. The toluene layer is condensed and the residue is applied to column chromatography on silica gel with acetone-hexane (1:20) as eluent. 9.07 g of a pale yellow oil are obtained (96%). 1H NMR (CDCl3), δ[ppm]: d 2.48 (s, 3H), 2.96 (s, 6H), 7.20 (s, 1H), 7.21 (d, 2H), 7.49 (d, 2H).

Workup

  1. temperatureheated
  2. temperatureto reflux for 2.5 hr
  3. temperatureafter cooling
  4. extractionthe product is extracted with toluene
  5. customcondensed

Sources & evidence

ORD record
ord-c09d484158534d5fa292a66f79acfbcd
Source dataset
uspto-grants-2003_07
Patent number
US06596445B1

Reaction notes

Loading…