Thionyl Chloride → HCID 21890740, compound

HRID 721594Notes

Reaction equation

HRID 721594 reaction equation
S(Cl)(Cl)=O.O(C(CC)C(O)=O)C1C=CC=CC=1.O(C(CC)C(Cl)=O)C1C=CC=CC=1.[O:31]([CH:38]([CH2:44][CH3:45])[C:39]([N:41]=[C:42]=[S:43])=[O:40])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.[Cl:46][C:47]1[CH:48]=[C:49]([CH:51]=[CH:52][C:53]=1[O:54][C:55]1[C:64]2[C:59](=[CH:60][C:61]([O:67][CH3:68])=[C:62]([O:65][CH3:66])[CH:63]=2)[N:58]=[CH:57][CH:56]=1)[NH2:50]>C(O)C.C1(C)C=CC=CC=1>[Cl:46][C:47]1[CH:48]=[C:49]([NH:50][C:42]([NH:41][C:39](=[O:40])[CH:38]([O:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:44][CH3:45])=[S:43])[CH:51]=[CH:52][C:53]=1[O:54][C:55]1[C:64]2[C:59](=[CH:60][C:61]([O:67][CH3:68])=[C:62]([O:65][CH3:66])[CH:63]=2)[N:58]=[CH:57][CH:56]=1

Participants

8

Reactant 5

HCID 24386Thionyl ChlorideHCID 579872-Phenoxybutanoic acidHCID 30848382-Phenoxybutanoyl chlorideHCID 117390273-Chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]anilineHCID 21891125HCID 21891125, compound

Product 1

HCID 21890740HCID 21890740, compoundYield 27%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 1140TolueneSolvent2×

Conditions

Temperature
100 °C

Procedure

Toluene (20 ml) and thionyl chloride (1 ml) were added to commercially available 2-phenoxybutanoic acid (80 mg), and the mixture was heated at 100° C. for one hr. The solvent was removed by distillation, and 2-phenoxybutanoyl isothiocyanate was prepared using the resultant 2-phenoxybutanoyl chloride as a starting compound according to the description of the literature. 2-Phenoxybutanoyl isothiocyanate thus obatined was dissolved in ethanol (1 ml) to prepare a solution. 3-Chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]aniline (50 mg), toluene (5 ml), and ethanol (1 ml) were added to the solution, and the mixture was stirred at room temperature for 16 hr. The reaction solution was concentrated, and the residue was purified by chromatography on silica gel using chloroform/acetone for development to give the title compound (25 mg, yield 27%).

Workup

  1. customThe solvent was removed by distillation, and 2-phenoxybutanoyl isothiocyanate
  2. customwas prepared
  3. customto prepare a solution
  4. concentrationThe reaction solution was concentrated
  5. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-119b117dbd754e4f90a9320236093da7
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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