Diethylamine → HCID 86634497、化合物

Air in a 20 ml Schlenk tube was replaced by Ar gas and 1.02 g (7 mmol) of m-ethynylbenzoic acid and 5 g (42 mmol) of thionyl chloride were added to the tube and the mixture was stirred at 50° C. for 2 hours and then excess thionyl chloride was removed by distillation under reduced pressure to obtain m-ethynylbenzoyl chloride. To the m-ethynylbenzoyl chloride obtained was added a solution having 1.49 ml (14.4 mmol) of diethylamine dissolved in 7 ml of dichloromethane under ice-cooling and then the resultant mixture was stirred at room temperature for one hour. After completion of the stirring, dichloromethane was removed by distillation under reduced pressure and 35 ml of water was added to the resultant residue. The mixture was extracted with 35 ml of diethyl ether, the ether layer was dried over magnesium sulfate and the solvent was removed by distillation under reduced pressure using an evaporator. The resultant crude reaction product was purified by column chromatography (Hexane/AcOEt=5/1 to 3/1) using silica gel to obtain 1.3 g of 3-ethynyl-N,N-diethylbenzamide which is a desired product as pale yellow liquid. (Yield: 92%)

1. additionwas added a solution
2. temperaturecooling
3. customAfter completion of the stirring, dichloromethane was removed by distillation under reduced pressure and 35 ml of water
4. additionwas added to the resultant residue
5. extractionThe mixture was extracted with 35 ml of diethyl ether
6. dry with materialthe ether layer was dried over magnesium sulfate
7. customthe solvent was removed by distillation under reduced pressure
8. customan evaporator
9. customThe resultant crude reaction product
10. customwas purified by column chromatography (Hexane/AcOEt=5/1 to 3/1)

ORDレコード

ord-57bb9f5f0997448287babb22cd727af9

出典データセット

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07932398B2