Synthesis of methyl 2-azidoacetate

Preparation of methyl 2-azidoacetate

Preparation of methyl 2-azidoacetate

Preparation of methyl 2-azidoacetate

A solution of methyl chloroacetate (397 g, 3.65 M) in dry (sieves) acetonitrile (1.6 L) was treated with sodium azide (235 g, 3.63 M) under a nitrogen atmosphere and the mixture was heated for 20 hours at reflux. After cooling, water (600 mL) was added and stirred for 0.5 hours, the top layer was separated, and the bottom layer was treated with salt and extracted several times several times with ether. The saved top-layer and ether extracts were combined and the solvent removed in vacuo at a bath temperature not exceeding 50° C to give methyl 2-azidoacetate as a light amber oil (385 g, 93%1), 1H NMR(CDCl3): 6 3.81 (s, 3H), 3.94 (s, 2H); MS: m/z 83 (MH+). The isolated methyl 2-azidoacetate should be used without purification.

Synth. Commun. 1991, 21, 675.

J. Org. Chem., 1960, 25 (3), pp 387–390

Collect. Czech. Chem. Commun. 1978, 43, 1694.

Org. Synth. 2007, 84, 262.

IUPAC Name

methyl 2-azidoacetate

InChI

InChI=1S/C3H5N3O2/c1-8-3(7)2-5-6-4/h2H2,1H3

InChI Key

RXYCUKSOYJWGPE-UHFFFAOYSA-N

Canonical SMILES

COC(=O)CN=[N+]=[N-]

Depositor-Supplied Synonyms

Methyl 2-azidoacetate, 1816-92-8, Methyl azidoacetate, RXYCUKSOYJWGPE-UHFFFAOYSA-N, ST059604, methyl 3-diazo-3-azaprop-3-enoate, Azidoacetic acid, methyl ester, methyl azido-acetate, ACMC-20akir, AC1N2EBI, Azidoacetic acid methyl ester, azido-acetic acid methyl ester, SCHEMBL13482799, CTK4D7953, MolPort-004-946-784, ZERO/001819, Acetic acid, 2-azido-,methyl ester, SBB001917, AKOS005174463, ZINC100017103, MCULE-8257278223, NE54652, RP08144, TRA-0175394, OR036455, AB1007722, TR-039149, BB 0257904, FT-0685510, X5179, Aceticacid, azido-, methyl ester (7CI,9CI); Azidoacetic acid methyl ester; Methyl 2-azidoacetate; Methyl azidoacetate

Removed Synonyms

C3H5N3O2, CID4020482

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