Methylthiourea → HCID 178481679, compound

HRID 1291231Notes

Reaction equation

HRID 1291231 reaction equation
[Na].[CH3:2][NH:3][C:4]([NH2:6])=[S:5].[C:7]([CH:9]([CH2:15][CH:16](OCC)OCC)[C:10](OCC)=[O:11])#[N:8]>C(O)C>[CH3:2][N:3]1[C:7]2[NH:8][CH:16]=[CH:15][C:9]=2[C:10](=[O:11])[N:6]=[C:4]1[SH:5]

Participants

5

Reactant 3

HCID 2723704MethylthioureaHCID 4151505Ethyl 2-cyano-4,4-diethoxybutyrateHCID 5360545Sodium

Product 1

HCID 178481679HCID 178481679, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
50 °C

Procedure

Sodium metal (1.21 g) was dissolved in anhydrous ethanol (50 ml) followed by addition of N-methylthiourea (4.96 g), and the mixture was stirred for dissolution at 50° C. for 30 minutes. Then, a solution of ethyl 2-cyano-4,4-diethoxybutyrate (11.47 g) in ethanol (10 ml) was added and the mixture was refluxed at 100° C. for 5 hours. The solvent was then distilled off under reduced pressure and the residue was-dissolved by adding water (20 ml). Then, 10% hydrochloric acid (75 ml) was added and the mixture was stirred overnight. The resulting precipitate was collected by filtration, washed serially with water, ethanol and ether, and dried to provide the title compound (6.8 g). 1H-NMR (DMSO-d6) δ: 3.82(3H,s), 6.41-6.44(1H,m), 6.92-6.95(1H,s), 12.02(1H,s), 12.06(1H,s).

Workup

  1. temperaturethe mixture was refluxed at 100° C. for 5 hours
  2. distillationThe solvent was then distilled off under reduced pressure
  3. dissolutionthe residue was-dissolved
  4. additionby adding water (20 ml)
  5. additionThen, 10% hydrochloric acid (75 ml) was added
  6. stirringthe mixture was stirred overnight
  7. filtrationThe resulting precipitate was collected by filtration
  8. washwashed serially with water, ethanol and ether
  9. customdried

Sources & evidence

ORD record
ord-5b9885bfae4647a99253ec152fb1c4ca
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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