Triethylamine → HCID 22918594, compound

HRID 742284Notes

Reaction equation

HRID 742284 reaction equation
[CH2:1]([NH:4][CH2:5][C:6]([O:8]CC)=O)[C:2]#[CH:3].[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]=[C:19]=[S:20])=[C:14]([CH3:21])[CH:13]=1.C(N(CC)CC)C>C(Cl)Cl>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]2[C:6](=[O:8])[CH2:5][N:4]([CH2:1][C:2]#[CH:3])[C:19]2=[S:20])=[C:14]([CH3:21])[CH:13]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 900213-Chloro-6-isothiocyanatotolueneHCID 22918592HCID 22918592, compound

Product 1

HCID 22918594HCID 22918594, compoundYield 26.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of ethyl N-propargylaminoacetate (10.0 g), 4-chloro-2-methylphenylisothiocyanate (12.9 g), triethylamine (7.1 g), and methylene chloride (150 mL) was heated at reflux for 3 hours. The reaction mixture was cooled to ambient temperature, washed with 1 N HCl (100 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 Hexane-EtOAc afford the title compound (5.2 g) as yellow solid, m.p. 99°-102° C. Anal. Calcd. for. C13H11N2O Cl S: C, 56.01; H, 3.98; N, 10.05. Found: C, 55.61; H, 3.83; N, 10.0. Mass spectrum (EI, M.+) m/z 278.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. washwashed with 1 N HCl (100 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 Hexane-EtOAc

Sources & evidence

ORD record
ord-c3ea7bf6057a49029704417e469d422c
Source dataset
uspto-grants-1996_09
Patent number
US05554607

Reaction notes

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