ChemicalBook CAS DataBase List Hydrazinecarboxylic acid, 2-(2-propenyl)-, 1,1-dimethylethyl ester (9CI)

Hydrazinecarboxylic acid, 2-(2-propenyl)-, 1,1-dimethylethyl ester (9CI) synthesis

7synthesis methods

Product Name:Hydrazinecarboxylic acid, 2-(2-propenyl)-, 1,1-dimethylethyl ester (9CI)
CAS Number:192725-90-9
Molecular formula:C8H16N2O2
Molecular Weight:172.22

870-46-2 Synthesis

870-46-2
538 suppliers
$5.00/10g

106-95-6 Synthesis

106-95-6
424 suppliers
$10.00/5g

Hydrazinecarboxylic acid, 2-(2-propenyl)-, 1,1-dimethylethyl ester (9CI)

192725-90-9
5 suppliers
inquiry

Yield:192725-90-9 76%

Reaction Conditions:

Stage #1: t-butoxycarbonylhydrazinewith sodium hydride in N,N-dimethyl-formamide at -10;
Stage #2: allyl bromide in DMF (N,N-dimethyl-formamide) at 20;
Stage #3: with sodium dihydrogenphosphate in DMF (N,N-dimethyl-formamide);water;

Steps:

17.A

Stage A 50 g of BOC-NH-NH₂ is dissolved in 250 ml of anhydrous DMF into a flask placed under an inert atmosphere. The reaction medium is cooled down to -10° C., then 16.5 g of sodium hydride at 50% in oil is added by small fractions. Then propylene bromide is added and the reaction medium is left under agitation overnight at ambient temperature. Then water and a 1M solution of sodium hydrogen phosphate, then 200 ml of an AcOEt/heptane mixture 2/1 are added slowly, followed by extracting, drying the organic phase over magnesium sulphate, filtering and evaporating the solvent under reduced pressure. The crude product obtained is purified on silica eluding with a dichloromethane/AcOEt mixture 95/5. In this way 24 g of pure 1,1-dimethylethyl 2-(2-propenyl)-hydrazinecarboxylate is recovered. The corresponding yield is 76%.

References:

US2005/245505,2005,A1 Location in patent:Page/Page column 21

870-46-2 Synthesis

870-46-2
538 suppliers
$5.00/10g