Thionyl Chloride → 7-Amino-4-methylcoumarin-3-acetic chloride

HRID 1032022

Reaction equation

HRID 1032022 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:17])=[C:7]([CH2:13][C:14](O)=[O:15])[C:8](=[O:12])[O:9]2)=[CH:4][CH:3]=1.S(Cl)([Cl:20])=O>C1(C)C=CC=CC=1>[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:17])=[C:7]([CH2:13][C:14]([Cl:20])=[O:15])[C:8](=[O:12])[O:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 1293677-Amino-4-methylcoumarin-3-acetic acid

Product 1

HCID 221674557-Amino-4-methylcoumarin-3-acetic chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The reaction was carried out in a 500 ml two-necked reaction flask, containing 50 ml toluene, 7-amino-4-methylcoumarin-3-acetic acid (prepared as per Example 1 above), 699 mg (3 mmol) and thionyl chloride, 0.278 ml (446 ng, 3.75 mmol, BDH Chemicals, U.K.). Nitrogen was passed through the mixture during the reaction. The mixture was refluxed for 2 hours on an oil bath (temperature 130°-150° C.). The solvent was removed by rotatory evaporation and the precipitate was dried in vacuo.

Workup

  1. customThe reaction was carried out in a 500 ml two-necked reaction flask
  2. customNitrogen was passed through the mixture during the reaction
  3. temperatureThe mixture was refluxed for 2 hours on an oil bath (temperature 130°-150° C.)
  4. customThe solvent was removed by rotatory evaporation
  5. customthe precipitate was dried in vacuo

Sources & evidence

ORD record
ord-d62d687f39ec4ef9b6da278b9d964beb
Source dataset
uspto-grants-1990_09
Patent number
US04956480

Linked notes

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