Water → HCID 15565693, compound

HRID 1990069Notes

Reaction equation

HRID 1990069 reaction equation
C(O[C:4](=[C:7]([C:10]#[N:11])[C:8]#[N:9])[CH2:5][CH3:6])C.[C:12]([O:16][CH2:17][CH3:18])(=[O:15])[CH2:13][SH:14].C([O-])(=O)C.[K+].O>C(O)C>[CH2:17]([O:16][C:12]([C:13]1[S:14][C:4]([CH2:5][CH3:6])=[C:7]([C:8]#[N:9])[C:10]=1[NH2:11])=[O:15])[CH3:18]

Participants

6

Reactant 4

HCID 962WaterHCID 12185Ethyl ThioglycolateHCID 2314702-(1-Ethoxypropylidene)malononitrileHCID 517044Potassium Acetate

Product 1

HCID 15565693HCID 15565693, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

Add 2-(1-ethoxy-propylidene)-malononitrile, prepared in preparation 38, (230.0 g, 1531 mmol) in ethanol (1.3 L) stir with overhead stirring under nitrogen at rt and add ethyl thioglycolate (168.8 mL, 1531 mmol) and potassium acetate (225.4 g, 2297 mmol). Heat the resulting red mixture at 60° C. for 2 h. Add water (300 mL) and cool the mixture to 5° C. for 1 h. Collect the precipitate that forms by filtration, wash with 20-25% water/ethanol, and dry at rt for 3 d affording the title compound as light orange needles: 1H NMR (DMSO-d6) δ 6.76 (bs, 2H), 4.18 (q, J=7.1, 2H), 2.86 (q, J=7.5, 2H), 1.223 (t, J=7.1, 3H), 1.220 (t, J=7.5, 3H); 13C NMR (DMSO-d6) 163.8, 163.7, 153.7, 112.9, 100.0, 96.3, 60.0, 23.2, 14.3, 14.2.

Workup

  1. stirringstirring under nitrogen at rt
  2. customCollect the precipitate that forms
  3. filtrationby filtration
  4. washwash with 20-25% water/ethanol
  5. customdry at rt for 3 d

Sources & evidence

ORD record
ord-daf6f225cd3f46c18ecc837f65a86d43
Source dataset
uspto-grants-2010_01
Patent number
US07642361B2

Reaction notes

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