Toluene → HCID 21890632, compound

HRID 721591Notes

Reaction equation

HRID 721591 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[O:9][C:10]1[C:19]2[C:14](=[CH:15][C:16]([O:22][CH3:23])=[C:17]([O:20][CH3:21])[CH:18]=2)[N:13]=[CH:12][CH:11]=1)[NH2:5].C1(C)C=CC=CC=1.[CH2:31]([N:38]=[C:39]=[S:40])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C(O)C>[CH2:31]([NH:38][C:39]([NH:5][C:4]1[CH:6]=[CH:7][C:8]([O:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:22][CH3:23])=[C:17]([O:20][CH3:21])[CH:18]=3)[N:13]=[CH:12][CH:11]=2)=[C:2]([Cl:1])[CH:3]=1)=[S:40])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 2346Benzyl IsothiocyanateHCID 117390273-Chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]aniline

Product 1

HCID 21890632HCID 21890632, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

3-Chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]aniline (50 mg) was added to toluene (2 ml) and ethanol (2 ml) to prepare a solution. Benzyl isothiocyanate (48 μl) was then added to the solution, and the mixture was stirred at 80° C. for 6 hr. The reaction solution was concentrated, and ether and hexane were added to the residue. The resultant crystal was collected by filtration to give the title compound (46 mg, yield 65%).

Workup

  1. customto prepare a solution
  2. concentrationThe reaction solution was concentrated
  3. additionether and hexane were added to the residue
  4. filtrationThe resultant crystal was collected by filtration

Sources & evidence

ORD record
ord-522adcfd2ee24072967a99b608ceaeb0
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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