Triethylamine → HCID 19069744, compound

HRID 1957321Notes

Reaction equation

HRID 1957321 reaction equation
[CH2:1]([NH:3][CH2:4][C:5]([OH:7])=O)[CH3:2].[F:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([N:17]=[C:18]=[S:19])[CH3:16])=[CH:11][CH:10]=1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH2:1]([N:3]1[CH2:4][C:5](=[O:7])[N:17]([CH:15]([C:12]2[CH:13]=[CH:14][C:9]([F:8])=[CH:10][CH:11]=2)[CH3:16])[C:18]1=[S:19])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 316542N-EthylglycineHCID 5195361-Fluoro-4-(1-isothiocyanatoethyl)benzene

Product 1

HCID 19069744HCID 19069744, compoundYield 33.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of the crude N-ethyl glycine (18.4 g), 1-(4-fluorophenyl)-ethyl-isothiocyanate (18.1 g), triethyl amine (20.2 g) and chloroform (300 mL) was heated at reflux for 18 hours. The solvent was evaporated. The residue was dissolved in ethyl acetate (400 mL) and water (300 mL). The organic phase was washed with 1N HCl (2×300 mL), then evaporated to dryness. Crystallization from ethyl acetate afforded the title compound (8.8 g) as a light yellow solid, m.p. 93°-95° C. Anal. Calcd. for. C13H15F N2O S: C, 58.63; H, 5.68; N, 10.52. Found: C, 58.69; H, 5.64; N, 10.58. Mass spectrum (EI, M.+) m/z 266.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 hours
  3. customThe solvent was evaporated
  4. dissolutionThe residue was dissolved in ethyl acetate (400 mL)
  5. washThe organic phase was washed with 1N HCl (2×300 mL)
  6. customevaporated to dryness
  7. customCrystallization from ethyl acetate

Sources & evidence

ORD record
ord-5cee7a7d2cbc49778c00551f354cc2b6
Source dataset
uspto-grants-1998_07
Patent number
US05783707

Reaction notes

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