Sulfur dichloride → HCID 86619101, compound

HRID 2389222Notes

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:29]>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:29])=[O:22])[C:2]1=[O:3]

Participants

Conditions

Temperature: 35 °C

Procedure

After about 5 g of coumarin-oxyhexylbenzoic acid (compound 3) (about 13.075 mol, about 1 eq) was added to about 100 ml of methylene chloride under nitrogen atmosphere, about 1.71 g of thiochloride (about 14.383 mol, about 1.1 eq) was added thereto and the mixture was stirred at about 35° C. for about 5 hours. Then, the reaction mixture was subjected to evaporation to remove the solvent and recrystalized with ethylacetate/hexane, to obtain coumarin-oxyhexylbenzoyl chloride (compound 4).

Workup

customThen, the reaction mixture was subjected to evaporation
customto remove the solvent
customrecrystalized with ethylacetate/hexane

Sources & evidence

ORD record: ord-569d776393544aa29f0c90dab13830b6
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08273460B2

Reaction notes

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