Myristic Acid → HCID 21890170, compound

HRID 721849Notes

Reaction equation

HRID 721849 reaction equation
S(Cl)(Cl)=O.C(O)(=O)CCCCCCCCCCCCC.C(Cl)(=O)CCCCCCCCCCCCC.[C:37]([N:52]=[C:53]=[S:54])(=[O:51])[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50].[CH3:55][O:56][C:57]1[CH:58]=[C:59]2[C:64](=[CH:65][C:66]=1[O:67][CH3:68])[N:63]=[CH:62][CH:61]=[C:60]2[O:69][C:70]1[CH:76]=[CH:75][C:73]([NH2:74])=[CH:72][CH:71]=1>C(O)C.C1(C)C=CC=CC=1>[CH3:55][O:56][C:57]1[CH:58]=[C:59]2[C:64](=[CH:65][C:66]=1[O:67][CH3:68])[N:63]=[CH:62][CH:61]=[C:60]2[O:69][C:70]1[CH:71]=[CH:72][C:73]([NH:74][C:53]([NH:52][C:37](=[O:51])[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50])=[S:54])=[CH:75][CH:76]=1

Participants

8

Reactant 5

HCID 11005Myristic AcidHCID 24386Thionyl ChlorideHCID 66986Myristoyl chlorideHCID 115945434-[(6,7-Dimethoxyquinolin-4-yl)oxy]anilineHCID 21890402HCID 21890402, compound

Product 1

HCID 21890170HCID 21890170, compoundYield 60%

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 tetradecanoic acid (80 mg), and the mixture was heated at 100° C. for one hr. The solvent was removed by distillation, and tetradecanoyl isothiocyanate was prepared using the resultant tetradecanoyl chloride as a starting compound according to the description of the literature. Tetradecanoyl isothiocyanate was dissolved in ethanol (1 ml) to prepare a solution. 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 2 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 (58 mg, yield 60%).

Workup

  1. customThe solvent was removed by distillation, and tetradecanoyl 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-af019965d60e480aa034fe25786426dd
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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