4-Phenylbutyric Acid → HCID 21890750, compound

HRID 721913Notes

Reaction equation

HRID 721913 reaction equation
S(Cl)(Cl)=O.C1(CCCC(O)=O)C=CC=CC=1.C1(CCCC(Cl)=O)C=CC=CC=1.[CH3:29][O:30][C:31]1[CH:32]=[C:33]2[C:38](=[CH:39][C:40]=1[O:41][CH3:42])[N:37]=[CH:36][N:35]=[C:34]2[O:43][C:44]1[CH:50]=[CH:49][C:47]([NH2:48])=[CH:46][CH:45]=1.[C:51]1([CH2:57][CH2:58][CH2:59][C:60]([N:62]=[C:63]=[S:64])=[O:61])[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1>C1(C)C=CC=CC=1.C(O)C>[CH3:29][O:30][C:31]1[CH:32]=[C:33]2[C:38](=[CH:39][C:40]=1[O:41][CH3:42])[N:37]=[CH:36][N:35]=[C:34]2[O:43][C:44]1[CH:50]=[CH:49][C:47]([NH:48][C:63]([NH:62][C:60](=[O:61])[CH2:59][CH2:58][CH2:57][C:51]2[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=2)=[S:64])=[CH:46][CH:45]=1

Participants

8

Reactant 5

HCID 47754-Phenylbutyric AcidHCID 24386Thionyl ChlorideHCID 116163634-(6,7-Dimethoxyquinazolin-4-yloxy)anilineHCID 117898654-Phenylbutanoyl ChlorideHCID 21890360HCID 21890360, compound

Product 1

HCID 21890750HCID 21890750, compoundYield 45%

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 4-phenylbutanoic acid (80 mg), and the mixture was heated at 100° C. for one hr. The solvent was removed by distillation, and 4-phenylbutanoyl isothiocyanate was prepared using the resultant 4-phenylbutanoyl chloride as a starting compound according to the description of the literature. 4-[(6,7-Dimethoxy-4-quinazolinyl)oxy]aniline (50 mg) was dissolved in toluene (5 ml) and ethanol (1 ml) to prepare a solution. A solution of 4-phenylbutanoyl isothiocyanate in ethanol (1 ml) was then 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 (37 mg, yield 45%).

Workup

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

Sources & evidence

ORD record
ord-d213f749c1e646f5b48128bc618358b5
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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