Ethyl cyanoacetate → HCID 19616892, compound

HRID 31061Notes

Reaction equation

HRID 31061 reaction equation
C[O-].[Na+].[CH3:4][O:5][CH2:6][CH2:7][CH2:8][NH:9][C:10]([NH2:12])=[S:11].[C:13]([CH2:15][C:16](OCC)=[O:17])#[N:14]>C(O)C>[NH2:14][C:13]1[N:9]([CH2:8][CH2:7][CH2:6][O:5][CH3:4])[C:10](=[S:11])[NH:12][C:16](=[O:17])[CH:15]=1

Participants

5

Reactant 3

HCID 7764Ethyl cyanoacetateHCID 27740941-(3-Methoxypropyl)-2-thioureaHCID 10942334Sodium Methoxide

Product 1

HCID 19616892HCID 19616892, compoundYield 48.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Sodium methoxide (0.81 g, 21.2 mmol, 1.05 eq.) was added to a solution of 3-methoxypropylthiourea (3.00 g, 20.2 mmol) in ethanol (10 mL). Ethyl cyanoacetate (2.18 mL, 20.2 mmol) in ethanol (10 mL) was added and the resulting white slurry was heated to reflux for 2.5 h. The solvent was evaporated and the remaining pale brown oil was treated with 2M acetic acid (15 mL,). The white crystals were filtered off and washed with acetic acid to give the title compound (2.10 g, 48%).

Workup

  1. temperaturethe resulting white slurry was heated
  2. temperatureto reflux for 2.5 h
  3. customThe solvent was evaporated
  4. additionthe remaining pale brown oil was treated with 2M acetic acid (15 mL,)
  5. filtrationThe white crystals were filtered off
  6. washwashed with acetic acid

Sources & evidence

ORD record
ord-cc6dcb2bbcda45e6942cf4787f9a8a66
Source dataset
uspto-grants-2008_09
Patent number
US07425560B2

Reaction notes

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