Acetic acid, azido-, ethyl ester → HCID 72644371, compound

HRID 1581659Notes

Reaction equation

[Na].[CH3:2][O:3][C:4]1[C:5]([CH:9]=O)=[CH:6][S:7][CH:8]=1.[N:11]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[N+:12]=[N-:13]>C(O)C.CCOCC.O>[CH2:18]([O:17][C:15](=[O:16])[C:14]([N:11]=[N+:12]=[N-:13])=[CH:9][C:5]1[C:4]([O:3][CH3:2])=[CH:8][S:7][CH:6]=1)[CH3:19]

Participants

Conditions

Temperature: -15 °C

Procedure

Sodium (20.0 g, 0.870 mol) was dissolved in absolute ethanol (550 mL) and the resulting solution cooled to −15° C. A mixture of 4-methoxy-3-thiophenaldehyde (32.4 g, 0.228 mol) and ethyl azidoacetate (118 g, 0.914 mol) in absolute ethanol (30 mL) and ether (30 mL) was added slowly such that the temperature of the reaction mixture did not rise above −10° C. The mixture warmed to −40° C. over 40 min accompanied by vigorous gas evolution. After 3 h the mixture was diluted with water (1 L) and the resulting precipitate was collected via vacuum filtration to provide 31.8 g (55%) of the title compound. Recrystallization (hexanes) of an analytical sample provided yellow crystals: mp 88-90° C. 1H NMR (CDCl3) 88.14 (d, J=3.3 Hz, 1H), 6.94 (s, 1H), 6.19 (d, J=3.3 Hz, 1H), 4.35 (q, J=7.0 Hz, 2H), 3.86 (s, 3H), 1.41 (t, J=7.0 Hz, 3H); MS ES+m/e 254 (p+1); IR (KBr, cm−1) 2114, 1700, 1256. Anal. Calcd for C10H11N3O3S: C, 47.42; H, 4.38; N, 16.59. Found: C, 47.09; H, 4.46; N, 15.87.

Workup

additionwas added slowly such that the temperature of the reaction mixture
customdid not rise above −10° C
temperatureThe mixture warmed to −40° C. over 40 min
filtrationthe resulting precipitate was collected via vacuum filtration

Sources & evidence

ORD record: ord-5c07cdba83ba47dd88d36ed5249a35e7
Source dataset: uspto-grants-2004_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06730694B1

Reaction notes

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