Ammonia → 4-Methyl-1,2-dithiolane-4-carboxamide

HRID 1915986Notes

Reaction equation

HRID 1915986 reaction equation
ClC(OCC(C)C)=O.[CH3:9][C:10]1([C:15]([OH:17])=O)[CH2:14][S:13][S:12][CH2:11]1.C([N:20](CC)CC)C.N>C1COCC1.O.C(O)(C)C>[CH3:9][C:10]1([C:15]([NH2:20])=[O:17])[CH2:14][S:13][S:12][CH2:11]1

Participants

8

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 200693114-Methyl-1,2-dithiolane-4-carboxylic acid

Product 1

HCID 263703824-Methyl-1,2-dithiolane-4-carboxamideYield 60%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Alternatively, method (Ex. 5-b), 1.2 equivalents of isobutyl chloroformate are added, at 0° C., to a solution of 1 g of Compound 1 in THF with 1.2 equivalents of triethylamine. After 2 hours at room temperature, the reaction medium is added to a cooled solution of ammonia, either at 28% in water or at 2N in isopropanol. The medium is stirred at room temperature for the time required, and then concentrated under vacuum. The crude product is then taken up in toluene, to give Compound 2 after precipitation. Yield=60%

Workup

  1. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-f4d03334d3fa43a1bfda756d39852eb9
Source dataset
uspto-grants-2013_12
Patent number
US08617524B2

Reaction notes

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