Ethyl Acetoacetate → HCID 21109090, compound

HRID 1766078Notes

Reaction equation

HRID 1766078 reaction equation
S(O)(O)(=O)=O.[CH3:6][S:7][C:8](=[NH:10])[NH2:9].[CH3:11][O:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH:16]=O.[C:21]([O:27][CH2:28][CH3:29])(=[O:26])[CH2:22][C:23]([CH3:25])=O.[Na]>CN(C=O)C.C(OCC)C>[CH3:6][S:7][C:8]1[NH:9][C:23]([CH3:25])=[C:22]([C:21]([O:27][CH2:28][CH3:29])=[O:26])[CH:16]([C:15]2[CH:18]=[CH:19][CH:20]=[C:13]([O:12][CH3:11])[CH:14]=2)[N:10]=1

Participants

7

Reactant 4

HCID 8868Ethyl AcetoacetateHCID 115693-MethoxybenzaldehydeHCID 752702-Methyl-2-thiopseudourea sulfateHCID 5360545Sodium

Product 1

HCID 21109090HCID 21109090, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of S-methylisothiourea sulfate (13.9 g), 3-methoxybenzaldehyde (7.5 g), ethyl acetoacetate (6.5 g) and sodium hydrogenocarbonate (21 g) in DMF (200 ml) was stirred at 70° C. for 18 h. The reaction mixture was cooled to room temperature, diluted with diethylether and washed with H2O and sat. aq. NaCl. The title compound was purified by chromatography on silica gel with hept/EtOAc=3/2 (v/v) as eluent.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washwashed with H2O and sat. aq. NaCl
  3. customThe title compound was purified by chromatography on silica gel with hept/EtOAc=3/2 (v/v) as eluent

Sources & evidence

ORD record
ord-27f09a2265e24b28b38f260d77eb7732
Source dataset
uspto-grants-2007_06
Patent number
US07229990B2

Reaction notes

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