Triethylamine → HCID 9838037, compound

HRID 742282Notes

Reaction equation

HRID 742282 reaction equation
[CH2:1]([NH:4][CH2:5][C:6]([O:8]CC)=O)[C:2]#[CH:3].[CH3:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[C:13]=1[N:19]=[C:20]=[S:21].C(N(CC)CC)C>C(Cl)Cl>[CH3:18][C:14]1[CH:15]=[CH:16][CH:17]=[C:12]([CH3:11])[C:13]=1[N:19]1[C:6](=[O:8])[CH2:5][N:4]([CH2:1][C:2]#[CH:3])[C:20]1=[S:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 879762,6-Xylyl isothiocyanateHCID 22918592HCID 22918592, compound

Product 1

HCID 9838037HCID 9838037, compoundYield 48.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of ethyl N-propargylaminoacetate (14.1 g), 2,6-dimethylphenylisothiocyanate (16.3 g), triethylamine (10.1 g), and methylene chloride (150 mL) was heated at reflux for 3 hours. The reaction mixture was cooled to ambient temperature, washed with 1N HCl (100 mL), then with water. The organic layer was separated, dried over anhydrous magnesium sulfate, then evaporated to dryness. The residual oil was triturated with hexane. The solid w, as collected by filtration. Recrystallization from hexane-EtOAc afforded the title compound (12.5 g) as yellow solid, m.p. 117°-121° C. Anal. Calcd. for. C14H14N2S2O: C, 65.09; H, 5.46; N, 10.84. Found: C, 65.23; H, 5.43; N, 10.88. Mass spectrum (EI, M.+) m/z 258.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. washwashed with 1N HCl (100 mL)
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated to dryness
  7. customThe residual oil was triturated with hexane
  8. filtrationThe solid w, as collected by filtration
  9. customRecrystallization from hexane-EtOAc

Sources & evidence

ORD record
ord-68977faf32664bccbea9ab4ec591c624
Source dataset
uspto-grants-1996_09
Patent number
US05554607

Reaction notes

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