Hydrochloric Acid → HCID 57975292, compound

HRID 1865047Notes

Reaction equation

HRID 1865047 reaction equation
[O-]CC.[Na+].Cl.[CH2:6]([O:8][C:9](=[O:13])[CH2:10][NH:11][CH3:12])[CH3:7].C(O[C:17](=[C:20]([C:23]#[N:24])[C:21]#[N:22])[CH2:18][CH3:19])C.Cl>C(O)C>[CH2:6]([O:8][C:9]([C:10]1[N:11]([CH3:12])[C:17]([CH2:18][CH3:19])=[C:20]([C:21]#[N:22])[C:23]=1[NH2:24])=[O:13])[CH3:7]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 171173Ethyl N-methylaminoacetate hydrochlorideHCID 2314702-(1-Ethoxypropylidene)malononitrileHCID 2723922Sodium ethoxide

Product 1

HCID 57975292HCID 57975292, compoundYield 66.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Conditions

Temperature
15 °C

Procedure

Alternatively the title compound may be prepared by the following procedure. Charge ethanol (3.40 L, denatured with 0.5% toluene) to a 22 L 3-neck reaction flask equipped with a mechanical stirrer, condenser, addition funnel and cooling bath. Cool the ethanol to 8° C. and add sodium ethoxide (805 grams, 11.35 mol) portion-wise over 20 minutes. In a separate flask, combine sarcosine ethyl ester hydrochloride (697 g, 4.54 mol), 2-(1-ethoxy-propylidene)-malononitrile (681 grams, 4.54 mol, prepared in preparation 35) and ethanol (3.0 L) and stir to dissolve the solids. Add the resulting solution to the 22 L flask over 33 minutes while maintaining about 11 C. Maintain the reaction mixture between 10-20° C. for 3.5 hours. Stir the mixture at room temperature overnight, then cool to 1° C. Adjust the pH to 7.0 by adding 1 N HCl (6.58 L) and stir the resulting suspension at 0-5° C. for 3 hours. Collect the precipitate by filtration, rinse the filter cake with deionized water (1.0 L) and vacuum-dry at 40° C., to afford the title compound in 66.7% yield. Mass spectrum (m/e): 222.4 (M+1).

Workup

  1. temperaturecooling bath
  2. customIn a separate flask, combine
  3. dissolutionto dissolve the solids
  4. additionAdd the resulting solution to the 22 L flask over 33 minutes
  5. temperaturewhile maintaining about 11 C
  6. temperaturecool to 1° C
  7. stirringstir the resulting suspension at 0-5° C. for 3 hours
  8. customCollect the precipitate
  9. filtrationby filtration
  10. washrinse the filter cake with deionized water (1.0 L)
  11. customvacuum-dry at 40° C.

Sources & evidence

ORD record
ord-a515ec8926eb496aa1091f8434c7a9e4
Source dataset
uspto-grants-2009_12
Patent number
US07625932B2

Reaction notes

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