Thionyl Chloride → HCID 21890100, compound

HRID 721917Notes

Reaction equation

HRID 721917 reaction equation
S(Cl)(Cl)=O.ClC1C=CC=CC=1OC(C)C(O)=O.ClC1C=CC=CC=1OC(C)C(Cl)=O.[CH3:31][O:32][C:33]1[CH:34]=[C:35]2[C:40](=[CH:41][C:42]=1[O:43][CH3:44])[N:39]=[CH:38][N:37]=[C:36]2[O:45][C:46]1[CH:52]=[CH:51][C:49]([NH2:50])=[CH:48][CH:47]=1.[Cl:53][C:54]1[CH:67]=[CH:66][CH:65]=[CH:64][C:55]=1[O:56][CH:57]([CH3:63])[C:58]([N:60]=[C:61]=[S:62])=[O:59]>C1(C)C=CC=CC=1.C(O)C>[Cl:53][C:54]1[CH:67]=[CH:66][CH:65]=[CH:64][C:55]=1[O:56][CH:57]([CH3:63])[C:58]([NH:60][C:61]([NH:50][C:49]1[CH:51]=[CH:52][C:46]([O:45][C:36]2[C:35]3[C:40](=[CH:41][C:42]([O:43][CH3:44])=[C:33]([O:32][CH3:31])[CH:34]=3)[N:39]=[CH:38][N:37]=2)=[CH:47][CH:48]=1)=[S:62])=[O:59]

Participants

8

Reactant 5

HCID 24386Thionyl ChlorideHCID 72862Propanoic acid, 2-(2-chlorophenoxy)-HCID 116163634-(6,7-Dimethoxyquinazolin-4-yloxy)anilineHCID 15006563HCID 15006563, compoundHCID 21890746HCID 21890746, compound

Product 1

HCID 21890100HCID 21890100, compoundYield 50%

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-(2-chlorophenoxy)propanoic acid (80 mg), and the mixture was heated at 100° C. for one hr. The solvent was removed by distillation, and 2-(2-chlorophenoxy)propanoyl isothiocyanate was prepared using the resultant 2-(2-chlorophenoxy)propanoyl 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 2-(2-chlorophenoxy)propanoyl 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 (45 mg, yield 50%).

Workup

  1. customThe solvent was removed by distillation, and 2-(2-chlorophenoxy)propanoyl 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-beb41c6ed1454281878fe2d21d74cd65
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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