Thionyl Chloride → HCID 13927511, compound

HRID 1419036Notes

Reaction equation

HRID 1419036 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

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 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]amino-diphenyl methanol as an oily product.

Workup

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

Sources & evidence

ORD record
ord-47c41e6598a24283a0f4fd66fd6ec814
Source dataset
uspto-grants-1999_03
Patent number
US05885979

Reaction notes

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