Thionyl Chloride → HCID 21891198, compound

HRID 721912Notes

Reaction equation

HRID 721912 reaction equation
S(Cl)(Cl)=O.CC1C=CC=CC=1OCC(O)=O.CC1C=CC=CC=1OCC(Cl)=O.[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.[CH3:51][C:52]1[CH:64]=[CH:63][CH:62]=[CH:61][C:53]=1[O:54][CH2:55][C:56]([N:58]=[C:59]=[S:60])=[O:57]>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:59]([NH:58][C:56](=[O:57])[CH2:55][O:54][C:53]2[CH:61]=[CH:62][CH:63]=[CH:64][C:52]=2[CH3:51])=[S:60])=[CH:46][CH:45]=1

Participants

8

Reactant 5

HCID 24386Thionyl ChlorideHCID 746512-(2-Methylphenoxy)acetic acidHCID 116163634-(6,7-Dimethoxyquinazolin-4-yloxy)anilineHCID 12353488(2-Methylphenoxy)acetyl chlorideHCID 12353491(2-Methylphenoxy)acetyl isothiocyanate

Product 1

HCID 21891198HCID 21891198, compoundYield 44%

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-methylphenoxy)acetic acid (80 mg), and the mixture was heated at 100° C. for one hr. The solvent was removed by distillation, and 2-(2-methylphenoxy)ethanoyl isothiocyanate was prepared using the resultant 2-(2-methylphenoxy)ethanoyl 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-methylphenoxy)ethanoyl 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 44%).

Workup

  1. customThe solvent was removed by distillation, and 2-(2-methylphenoxy)ethanoyl 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-d5552d74354e4476afcf6d37f4fc2169
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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