Triethylamine → HCID 11229535, compound

HRID 742226Notes

Reaction equation

HRID 742226 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-43b07feeff074ae09b3539272d98e8e7
Source dataset
uspto-grants-1996_09
Patent number
US05554607

Reaction notes

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