Thionyl Chloride → HCID 21891024, compound

HRID 721767Notes

Reaction equation

HRID 721767 reaction equation
S(Cl)(Cl)=O.C1(C2C=CC(C(O)=O)=CC=2)C=CC=CC=1.C1(C2C=CC(C(Cl)=O)=CC=2)C=CC=CC=1.[CH3:35][O:36][C:37]1[CH:38]=[C:39]2[C:44](=[CH:45][C:46]=1[O:47][CH3:48])[N:43]=[CH:42][CH:41]=[C:40]2[O:49][C:50]1[CH:56]=[CH:55][C:53]([NH2:54])=[CH:52][C:51]=1[F:57].[C:58]1([C:64]2[CH:69]=[CH:68][C:67]([C:70]([N:72]=[C:73]=[S:74])=[O:71])=[CH:66][CH:65]=2)[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1>C1(C)C=CC=CC=1.C(O)C>[CH3:35][O:36][C:37]1[CH:38]=[C:39]2[C:44](=[CH:45][C:46]=1[O:47][CH3:48])[N:43]=[CH:42][CH:41]=[C:40]2[O:49][C:50]1[CH:56]=[CH:55][C:53]([NH:54][C:73]([NH:72][C:70](=[O:71])[C:67]2[CH:68]=[CH:69][C:64]([C:58]3[CH:59]=[CH:60][CH:61]=[CH:62][CH:63]=3)=[CH:65][CH:66]=2)=[S:74])=[CH:52][C:51]=1[F:57]

Participants

8

Reactant 5

HCID 24386Thionyl ChlorideHCID 66724(1,1'-Biphenyl)-4-carboxylic acidHCID 841514-Phenylbenzoyl chlorideHCID 114269974-((6,7-Dimethoxyquinolin-4-yl)oxy)-3-fluorobenzenamineHCID 1247221167132-17-6

Product 1

HCID 21891024HCID 21891024, compoundYield 92%

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-phenylbenzoic acid (80 mg), and the mixture was heated at 100° C. for one hr. The solvent was removed by distillation, and 4-phenyl-1-benzenecarbonyl isothiocyanate was prepared using the resultant 4-phenyl-1-benzenecarbonyl chloride as a starting compound according to the description of the literature. 4-[(6,7-Dimethoxy-4-quinolyl)oxy]-3-fluoroaniline (50 mg) was dissolved in toluene (5 ml) and ethanol (1 ml) to prepare a solution. A solution of 4-phenyl-1-benzenecarbonyl 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 (76 mg, yield 92%). Mass spectrometry value (ESI-MS, m/z): 554 (M++1)

Workup

  1. customThe solvent was removed by distillation, and 4-phenyl-1-benzenecarbonyl 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-ec60e904ac0b4ac1a14d7f9ba0e10ec7
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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