Triethylamine → HCID 11229535, compound

HRID 1957313Notes

Reaction equation

HRID 1957313 reaction equation
Cl.C([O:4][C:5](=O)[CH2:6][NH:7][CH3:8])C.[N:10]1[CH:15]=[CH:14][CH:13]=[C:12]([N:16]=[C:17]=[S:18])[CH:11]=1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH3:8][N:7]1[CH2:6][C:5](=[O:4])[N:16]([C:12]2[CH:11]=[N:10][CH:15]=[CH:14][CH:13]=2)[C:17]1=[S:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 171173Ethyl N-methylaminoacetate hydrochlorideHCID 27372423-Pyridyl isothiocyanate

Product 1

HCID 11229535HCID 11229535, compoundYield 39.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of sarcosine ethyl ester hydrochloride (7.68 g), pyridin-3-yl-isothiocyanate (6.8 g), triethyl amine (10.1 g) and chloroform (200 mL) was heated at reflux for 3.5 hours. The solvent was evaporated. The residue was dissolved in ethyl acetate (300 mL) and washed with water (2×200 mL). The organic phase was dried over anhydrous magnesium sulfate. The solvent was evaporated. Crystallization from ethyl acetate afforded the title compound (4.1 g) as an off-white solid, m.p. 149°-151°C. Anal. Calcd. for C9H9N3O S: C, 52.16; H, 4.38; N, 20.28. Found: C, 52.16; H, 4.05; N, 20.06. Mass spectrum (EI, M.+) m/z 207.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3.5 hours
  3. customThe solvent was evaporated
  4. dissolutionThe residue was dissolved in ethyl acetate (300 mL)
  5. washwashed with water (2×200 mL)
  6. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated
  8. customCrystallization from ethyl acetate

Sources & evidence

ORD record
ord-9c18f6e1135c4243b0df7278d5a2d06b
Source dataset
uspto-grants-1998_07
Patent number
US05783707

Reaction notes

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