Triethylamine → 2-Methyl-2-(2-thienyl)propionylazide

HRID 1940434Notes

Reaction equation

C(Cl)(=O)OCC.[CH3:7][C:8]([C:13]1[S:14][CH:15]=[CH:16][CH:17]=1)([CH3:12])[C:9](O)=[O:10].C(N(CC)CC)C.[N-:25]=[N+:26]=[N-:27].[Na+]>CC(C)=O.O>[CH3:7][C:8]([C:13]1[S:14][CH:15]=[CH:16][CH:17]=1)([CH3:12])[C:9]([N:25]=[N+:26]=[N-:27])=[O:10]

Participants

Conditions

Temperature: 0 °C

Procedure

10.6 ml of ethyl chlorocarbonate were gradually added, keeping the temperature below 0° C., to a solution of 15.8 g of 2-methyl-2-(2-thienyl)propionic acid [prepared as described in step (ii) above] and 15.6 ml of triethylamine in 210 ml of acetone. The reaction mixture was stirred at 0° C. for 2 hours, after which 110 ml of an aqueous solution containing 10.3 g of sodium azide were added to the mixture at 0° C. The reaction mixture was then stirred at 0° C. for 2 hours, diluted with water, and extracted three times with diethyl ether. The combined organic extracts were washed with 1N aqueous hydrochloric acid, with an aqueous solution of sodium hydrogencarbonate, and with a saturated solution of sodium chloride, in that order, after which it was dried over anhydrous magnesium sulfate, and concentrated by evaporation under reduced pressure to give 18.5 g of the title compound.

Workup

customthe temperature below 0° C.
additionwere added to the mixture at 0° C
stirringThe reaction mixture was then stirred at 0° C. for 2 hours
extractionextracted three times with diethyl ether
washThe combined organic extracts were washed with 1N aqueous hydrochloric acid, with an aqueous solution of sodium hydrogencarbonate
dry with materialwith a saturated solution of sodium chloride, in that order, after which it was dried over anhydrous magnesium sulfate
concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record: ord-3b74b69473404cc5ab25701126b5ebef
Source dataset: uspto-grants-1997_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05698720

Reaction notes

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