Dimethylformamide dimethyl acetal → Ethyl 3-(dimethylamino)-2-isocyanoacrylate

HRID 1267995Notes

Reaction equation

HRID 1267995 reaction equation
[N+:1]([CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])#[C-:2].CO[CH:11](OC)[N:12]([CH3:14])[CH3:13]>C(O)C>[CH2:7]([O:6][C:4](=[O:5])[C:3]([N+:1]#[C-:2])=[CH:11][N:12]([CH3:14])[CH3:13])[CH3:8]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 533707Ethyl isocyanoacetate

Product 1

HCID 54355309Ethyl 3-(dimethylamino)-2-isocyanoacrylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-carboalkoxythiazoles are prepared essentially according to the procedure of Schöllkopf, U., Porsch, P., Lau, H. Liebigs Ann. Chem. 1444 (1979). Thus, according to Method 55 and 56, reaction of ethyl isocyanoacetate with N,N-dimethylformamide dimethyl acetal in a suitable alcoholic solvent such as ethanol at room temperature gives the corresponding 3-dimethylamino-2-isocyano-acrylic acid ethyl ester. A solution of this compound in a suitable solvent such as tetrahydrofuran is treated with gaseous hydrogen sulfide in the presence of a suitable tertiary amine base such as triethylamine or diiso-propylethylamine or the like at room temperature to give the corresponding 4-carboethoxy-thiazole.

Sources & evidence

ORD record
ord-aaf729b004b1400888c74f141e9288e0
Source dataset
uspto-grants-2003_04
Patent number
US06555561B2

Reaction notes

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