Isobutylamine → HCID 9861386, compound

HRID 276286Notes

Reaction equation

HRID 276286 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:11]=[C:12]=[S:13].[CH2:14]([NH2:18])[CH:15]([CH3:17])[CH3:16].CCCCCC.[CH3:25][CH2:26][O:27]C(C)=O.CN1CCOCC1>CN(C=O)C>[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:11]=[C:12]1[N:18]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:26](=[O:27])[CH2:25][S:13]1

Participants

6

Reactant 4

HCID 6558IsobutylamineHCID 79724-MethylmorpholineHCID 1456212-Methyl-4-nitrophenyl isothiocyanateHCID 21226206Ethyl acetate hexane

Product 1

HCID 9861386HCID 9861386, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-methyl-4-nitrophenyl isothiocyanate (0.190 g, 1.0 mmol) in DMF (5.3 mL) was added isobutylamine (0.4 M solution in DMF, 5.3 mL) and the reaction mixture was allowed to stir for 4 h at which time TLC analysis (hexane:EtOAc 3:1) indicated consumption of the isothiocyanate. To the resulting mixture was added chloroacetic acid (0.8 M solution in DMF, 4.0 mL) followed by N-methylmorpholine (0.7 mL, 6.4 mmol). The reaction mixture was stirred at 80° C. for 18 h, then was partitioned between water (10 mL) and EtOAc (25 mL). The aqueous phase was back-extracted with EtOAc (2×10 mL). The combined organic layers were washed with a saturated NaCl solution (25 mL), dried (Na2SO4) and concentrated under reduced pressure. The resulting residue was purified by MPLC (Biotage 40 S silica gel column, gradient from 5% EtOAc/hex to 33% EtOAc/hex) to afford 2-(2-methyl-4-nitrophenylimino)-3-isobutyl-1,3-thiazolidin-4-one as a pale yellow oil (0.52 g, 85%).

Workup

  1. customconsumption of the isothiocyanate
  2. additionTo the resulting mixture was added chloroacetic acid (0.8 M solution in DMF, 4.0 mL)
  3. customwas partitioned between water (10 mL) and EtOAc (25 mL)
  4. extractionThe aqueous phase was back-extracted with EtOAc (2×10 mL)
  5. washThe combined organic layers were washed with a saturated NaCl solution (25 mL)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting residue was purified by MPLC (Biotage 40 S silica gel column, gradient from 5% EtOAc/hex to 33% EtOAc/hex)

Sources & evidence

ORD record
ord-93547073620d4a12abf1baf57f7d9f2c
Source dataset
uspto-grants-2002_03
Patent number
US06353006B1

Reaction notes

Loading…