Ethyl cyanoformate → Diethyl 2-[1-(toluene-4-sulfonyl)-1H-imidazol-4-yl]malonate

HRID 1666983Notes

Reaction equation

[C:1]1([CH3:21])[CH:6]=[CH:5][C:4]([S:7]([N:10]2[CH:14]=[C:13]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[N:12]=[CH:11]2)(=[O:9])=[O:8])=[CH:3][CH:2]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].C([C:34]([O:36][CH2:37][CH3:38])=[O:35])#N>C1COCC1>[C:1]1([CH3:21])[CH:2]=[CH:3][C:4]([S:7]([N:10]2[CH:14]=[C:13]([CH:15]([C:34]([O:36][CH2:37][CH3:38])=[O:35])[C:16]([O:18][CH2:19][CH3:20])=[O:17])[N:12]=[CH:11]2)(=[O:9])=[O:8])=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 1.000 g (3.243 mmol) of ethyl [1-(toluene-4-sulfonyl)-1H-imidazol-4-yl]-acetate was dissolved in 20 ml of THF and cooled to 0° C. Over a period of 10 min, 3.567 ml of lithium bis(trimethylsilyl)amide (3.567 mmol, 1M in THF) were added dropwise. This mixture was stirred at 0° C. for 30 min, 350 μl (3.567 mmol) of ethyl cyanoformate were then added and the mixture was stirred at RT for another 2 h. The reaction mixture was quenched with saturated ammonium chloride solution and extracted with ethyl acetate. The organic phase was washed with water and saturated NaCl solution, dried over Na2SO4, filtered and concentrated. Chromatography on silica gel (heptane/ethyl acetate 1:1) gave the title compound (0.390 g, 32%).

Workup

stirringthe mixture was stirred at RT for another 2 h
customThe reaction mixture was quenched with saturated ammonium chloride solution
extractionextracted with ethyl acetate
washThe organic phase was washed with water and saturated NaCl solution
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-41dda38ecaf3417a8701b38aed097dfe
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08044208B2

Reaction notes

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