Triethylamine → HCID 9838037, compound

HRID 1376867Notes

Reaction equation

HRID 1376867 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 was 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 was collected by filtration
  9. customRecrystallization from hexane-EtOAc

Sources & evidence

ORD record
ord-ea39c9cfa98748e8863fb1f756dadb32
Source dataset
uspto-grants-1997_09
Patent number
US05663363

Reaction notes

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