Triethylamine → HCID 22918593, compound

HRID 1376868Notes

Reaction equation

HRID 1376868 reaction equation
[CH2:1]([NH:4][CH2:5][C:6]([O:8]CC)=O)[C:2]#[CH:3].[Cl:11][C:12]1[CH:13]=[CH:14][C:15]([CH3:21])=[C:16]([N:18]=[C:19]=[S:20])[CH:17]=1.C(N(CC)CC)C>C(Cl)Cl>[Cl:11][C:12]1[CH:13]=[CH:14][C:15]([CH3:21])=[C:16]([N:18]2[C:6](=[O:8])[CH2:5][N:4]([CH2:1][C:2]#[CH:3])[C:19]2=[S:20])[CH:17]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 295195-Chloro-2-methylphenyl isothiocyanateHCID 22918592HCID 22918592, compound

Product 1

HCID 22918593HCID 22918593, compoundYield 36.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of ethyl N-propargylaminoacetate (7.0 g), 5-chloro-2-methylphenylisothiocyanate (9.2 g), triethylamine (5.0 g), and methylene chloride (100 mL) was heated at reflux for 3 hours. The reaction mixture was cooled to ambient temperature, washed with 1N HCl (50 mL), then with water. The organic layer was dried over anhydrous magnesium sulfate, then evaporated to dryness. The residual oil was triturated with hexane. The solid was collected by filtration. Recrystallization from EtOAc afforded the title compound (5.1 g) as a yellow solid, m.p. 131°-134° C. Anal. Calcd. for. C13H11N2O Cl S: C, 56.01; H, 3.98; N, 10.05. Found: C, 55.90; H, 3.77; N, 9.92. Mass spectrum (EI, M.+) m/z 278.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. washwashed with 1N HCl (50 mL)
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customevaporated to dryness
  6. customThe residual oil was triturated with hexane
  7. filtrationThe solid was collected by filtration
  8. customRecrystallization from EtOAc

Sources & evidence

ORD record
ord-c683f4a854d74bf7a1ce1dcfa839c458
Source dataset
uspto-grants-1997_09
Patent number
US05663363

Reaction notes

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