Diethyl Oxalate → HCID 18442534, compound

HRID 458691Notes

Reaction equation

[C:1]([O:8][CH2:9][CH3:10])(=[O:7])[C:2](OCC)=O.[CH2:11]([O:18][CH2:19][C:20]([O:22]CC)=O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[H-].[Na+].Cl.[NH2:28][C:29]1[S:30][CH2:31][CH2:32][N:33]=1>>[CH2:11]([O:18][C:19]1[C:20](=[O:22])[N:33]2[CH2:32][CH2:31][S:30][C:29]2=[N:28][C:2]=1[C:1]([O:8][CH2:9][CH3:10])=[O:7])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

Reactant 4

HCID 7268Diethyl Oxalate

HCID 24758Sodium hydride

HCID 290299Ethyl 2-(benzyloxy)acetate

HCID 5209263882-98-2

Product 1

HCID 18442534HCID 18442534, compoundYield 46%

Procedure

Reaction of diethyl oxalate (7.66 g, 52.4 mmol), ethyl benzyloxyacetate (10.2 g, 52.5 mmol) and sodium hydride (2.31 g of a 60% dispersion in mineral oil, 57.9 mmol) with 2-amino-2-thiazoline hydrochloride (7.28 g, 52.5 mmol) as described in intermediate 1 gave 7.99 g (46% yield) of the title ester as white crystals; mp 117 118° C. 1HNMR 400 MHz (CDCl3) δ (ppm): 1.32 (3H, t, J=7.1 Hz, CH3), 3.52 (2H, t, J=7.6 Hz, CH2), 4.34 (2H, q, J=7.1 Hz, OCH2), 4.49 (2H, t, J=7.6 Hz, CH2), 5.22 (2H, s, OCH2), 7.3–7.51 (5H, m, aromatics). Anal. Calcd for C16H16N2O4S: C, 57.81; H, 4.85; N, 8.42. Found: C, 57.78; H, 4.76; N, 8.30.

Sources & evidence

ORD record: ord-36adef3eff4f4fd29832ea8e2ad195c7
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07192948B2

Reaction notes

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