Triethylamine → HCID 18316261, compound

HRID 276288Notes

Reaction equation

HRID 276288 reaction equation
C(O[C:4](=[O:11])[CH2:5][NH:6][CH2:7][CH:8]([CH3:10])[CH3:9])C.CCN(CC)CC.[CH3:19][C:20]1[CH:25]=[C:24]([N+:26]([O-:28])=[O:27])[CH:23]=[CH:22][C:21]=1[N:29]=[C:30]=[S:31]>O.CC(C)=O>[CH3:19][C:20]1[CH:25]=[C:24]([N+:26]([O-:28])=[O:27])[CH:23]=[CH:22][C:21]=1[N:29]=[C:30]1[N:6]([CH2:7][CH:8]([CH3:9])[CH3:10])[CH2:5][C:4](=[O:11])[S:31]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 1456212-Methyl-4-nitrophenyl isothiocyanateHCID 10877410N-(2-Methylpropyl)glycine ethyl ester

Product 1

HCID 18316261HCID 18316261, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

A solution of N-isobutylglycine ethyl ester (0.41 g, 2.57 mmol) in water (5 mL) was treated with Et3N (0.71 mL, 5.15 mmol), followed by a solution of 2-methyl-4-nitrophenyl isothiocyanate (0.50 g, 2.57 mmol) in acetone (5 mL). The resulting mixture waxs heated at 40° C. for 2 h, then cooled to room temperature and concentrated under reduced pressure. The residue was separated between water (25 mL) and ethyl acetate (25 mL). The organic phase was dried (MgSO4) and concentrated under reduced pressure to afford 2-(2-methyl-4-nitrophenylimino)-3-isobutyl-1,3-thiazolidin-5-one (0.16 g, 88%): mp 152° C.

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was separated between water (25 mL) and ethyl acetate (25 mL)
  4. dry with materialThe organic phase was dried (MgSO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e3f547ecf3a6449d8dd628fda3a12da4
Source dataset
uspto-grants-2002_03
Patent number
US06353006B1

Reaction notes

Loading…