Ethyl bromopyruvate → HCID 69140342, compound

HRID 2183570Notes

Reaction equation

HRID 2183570 reaction equation
[CH3:1][C:2]1[S:6][C:5]([SH:7])=[N:4][N:3]=1.Br[CH2:9][C:10](=[O:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12]>C(Cl)Cl.C(#N)C>[CH2:14]([O:13][C:11](=[O:12])[C:10](=[O:16])[CH2:9][S:7][C:5]1[S:6][C:2]([CH3:1])=[N:3][N:4]=1)[CH3:15]

Participants

5

Reactant 2

HCID 66144Ethyl bromopyruvateHCID 178434161HCID 178434161, compound

Product 1

HCID 69140342HCID 69140342, compoundYield 91.3%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 5-methyl-1, 3,4-thiadiazole-2-thiol (264 mg, 2 mmol) and ethyl bromopyruvate (0.264 mL, 2.1 mmol) in methylene chloride (10 mL) and acetonitrile (10 mL) was stirred at 20° C. for 3 hours under nitrogen. The precipitates were filtered, washed with methylene chloride, and dried under vacuum. This gave the expected product, 3-(5-methyl-[1,3,4]thiadiazol-2-ylsulfanyl)-2-oxo-propionic acid ethyl ester (450 mg, yield 69%) as a solid. 1H-NMR (300 Hz, D3COD and d6-DMSO) δ (ppm): 4.22 (q, J=7.1 Hz, 2H), 3.78 (d, J=14.1 Hz, 1H), 3.71 (d, J=14.1 Hz, 1H), 2.74 (s, 3H), 1.27 (t, J=7.1 Hz, 3H).

Workup

  1. filtrationThe precipitates were filtered
  2. washwashed with methylene chloride
  3. customdried under vacuum

Sources & evidence

ORD record
ord-61bcf70f5ba347dabcb6dcae80ca412a
Source dataset
uspto-grants-2005_05
Patent number
US06900218B2

Reaction notes

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