Lauric Acid → HCID 21890774, compound

HRID 721848Notes

Reaction equation

HRID 721848 reaction equation
S(Cl)(Cl)=O.C(O)(=O)CCCCCCCCCCC.C(Cl)(=O)CCCCCCCCCCC.[C:33]([N:46]=[C:47]=[S:48])(=[O:45])[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44].[CH3:49][O:50][C:51]1[CH:52]=[C:53]2[C:58](=[CH:59][C:60]=1[O:61][CH3:62])[N:57]=[CH:56][CH:55]=[C:54]2[O:63][C:64]1[CH:70]=[CH:69][C:67]([NH2:68])=[CH:66][CH:65]=1>C(O)C.C1(C)C=CC=CC=1>[CH3:49][O:50][C:51]1[CH:52]=[C:53]2[C:58](=[CH:59][C:60]=1[O:61][CH3:62])[N:57]=[CH:56][CH:55]=[C:54]2[O:63][C:64]1[CH:65]=[CH:66][C:67]([NH:68][C:47]([NH:46][C:33](=[O:45])[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])=[S:48])=[CH:69][CH:70]=1

Participants

8

Reactant 5

HCID 3893Lauric AcidHCID 8166Dodecanoyl chlorideHCID 24386Thionyl ChlorideHCID 115945434-[(6,7-Dimethoxyquinolin-4-yl)oxy]anilineHCID 21890293HCID 21890293, compound

Product 1

HCID 21890774HCID 21890774, 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 dodecanoic acid (80 mg), and the mixture was heated at 100° C. for one hr. The solvent was removed by distillation, and dodecanoyl isothiocyanate was prepared using the resultant dodecanoyl chloride as a starting compound according to the description of the literature. Dodecanoyl 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 dodecanoyl 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-392c4fe4b593403ea3633052101e3604
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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