Thionyl Chloride → HCID 13927511, compound

HRID 1778Notes

Reaction equation

[Cl:1][CH:2]([CH2:6][CH:7]([C:9]([O:11][CH3:12])=[O:10])C)[C:3](O)=[O:4].S(Cl)([Cl:15])=O>>[Cl:1][CH:2]([CH2:6][CH2:7][C:9]([O:11][CH3:12])=[O:10])[C:3]([Cl:15])=[O:4]

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 867522202-Chloro-4-methoxycarbonyl valeric acid

Product 1

HCID 13927511HCID 13927511, compound

Procedure

A mixture of 6.2 g of 2-chloro-4-methoxycarbonyl valeric acid and 12.6 ml of thionyl chloride was refluxed for 30 minutes, then the solvent was distilled off under reduced pressure to leave 2-chloro-4-methoxycarbonyl butyryl chloride. A mixture of this product, 5.0 g of 2-benzylaminodiphenyl methanol, 100 ml of ethyl acetate and 100 ml of a saturated aqueous solution of sodium hydrogencarbonate was stirred for one hour at room temperature. The ethyl acetate layer was washed with water and dried over anhydrous magnesium sulfate. then the solvent was distilled off under reduced pressure. The residue was purified by means of a silica gel column chromatography (eluent, hexane:ethyl acetate=2:1) to give 5.3 g of 2-[N-benzyl-N-(2-chloro-4-methoxycarbonyl)butyryl]aminodiphenyl methanol as an oily product.

Workup

temperaturewas refluxed for 30 minutes
distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record: ord-a9d5932f47fc470faf0612928f6d7003
Source dataset: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05726306

Reaction notes

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