2-Methylvaleric acid → N-{3-Chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}-N'-(2-methylpentanoyl)thiourea

HRID 721952Notes

Reaction equation

HRID 721952 reaction equation
S(Cl)(Cl)=O.CC(CCC)C(O)=O.CC(CCC)C(Cl)=O.[CH3:21][CH:22]([CH2:28][CH2:29][CH3:30])[C:23]([N:25]=[C:26]=[S:27])=[O:24].[Cl:31][C:32]1[CH:33]=[C:34]([CH:36]=[CH:37][C:38]=1[O:39][C:40]1[C:49]2[C:44](=[CH:45][C:46]([O:52][CH3:53])=[C:47]([O:50][CH3:51])[CH:48]=2)[N:43]=[CH:42][CH:41]=1)[NH2:35]>C(O)C.C1(C)C=CC=CC=1>[Cl:31][C:32]1[CH:33]=[C:34]([NH:35][C:26]([NH:25][C:23](=[O:24])[CH:22]([CH3:21])[CH2:28][CH2:29][CH3:30])=[S:27])[CH:36]=[CH:37][C:38]=1[O:39][C:40]1[C:49]2[C:44](=[CH:45][C:46]([O:52][CH3:53])=[C:47]([O:50][CH3:51])[CH:48]=2)[N:43]=[CH:42][CH:41]=1

Participants

8

Reactant 5

HCID 73412-Methylvaleric acidHCID 24386Thionyl ChlorideHCID 1073852-Methylvaleryl chlorideHCID 117390273-Chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]anilineHCID 218904792-Methylpentanoyl isothiocyanate

Product 1

HCID 21891027N-{3-Chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}-N'-(2-methylpentanoyl)thioureaYield 94%

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-methylpentanoic acid (80 mg), and the mixture was heated at 100° C. for one hr. The solvent was removed by distillation, and 2-methylpentanoyl isothiocyanate was prepared using the resultant 2-methylpentanoyl chloride as a starting compound according to the description of the literature. The resultant 2-methylpentanoyl isothiocyanate 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 (69 mg, yield 94%).

Workup

  1. customThe solvent was removed by distillation, and 2-methylpentanoyl 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-e525d58f1bd44e74be3ea4546b6b9ba2
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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