Thionyl Chloride → HCID 86619101, compound

HRID 2243559Notes

Reaction equation

HRID 2243559 reaction equation
[O:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]2[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=2[C:21](O)=[O:22])[C:2]1=[O:3].S(Cl)([Cl:30])=O>C(Cl)Cl>[O:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]2[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=2[C:21]([Cl:30])=[O:22])[C:2]1=[O:3]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 86619102HCID 86619102, compound2×

Product 1

HCID 86619101HCID 86619101, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
35 °C

Procedure

Under a nitrogen atmosphere, about 5 g (about 13.075 mmol, about 1 eq) coumarin-oxyhexylbenzoic acid (compound 3) was put into about 100 ml of methylene chloride, and about 1.71 g of thionylchloride (about 14.383 mmol, about 1.1 eq) was added thereto, and the mixture was then stirred at about 35° C. for about 5 hours to form a reaction solution. Subsequently, a solvent was removed from the reaction solution, and then the residual was recrystallized using ethylacetate/hexane to obtain coumarin-oxyhexylbenzoyl chloride (compound 4).

Workup

  1. additionwas added
  2. customto form a reaction solution
  3. customSubsequently, a solvent was removed from the reaction solution
  4. customthe residual was recrystallized

Sources & evidence

ORD record
ord-db7623e87b3e41239c759ed129231fbe
Source dataset
uspto-grants-2010_03
Patent number
US07675059B2

Reaction notes

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