Triethylamine → 2-(2-Methyl-4-nitrophenylimino)-3-propanoyl-1,3-thiazolidine

HRID 276293Notes

Reaction equation

HRID 276293 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]1[NH:16][CH2:15][CH2:14][S:13]1.[C:17](Cl)(=[O:20])[CH2:18][CH3:19].CCN(CC)CC>C(Cl)Cl>[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:16]([C:17](=[O:20])[CH2:18][CH3:19])[CH2:15][CH2:14][S:13]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 178428748HCID 178428748, compound

Product 1

HCID 183160562-(2-Methyl-4-nitrophenylimino)-3-propanoyl-1,3-thiazolidineYield 35%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-(2-methyl-4-nitrophenylimino)-1,3-thiazolidine (prepared in a manner analogous to that described in Method C1a; 0.084 g, 0.35 mmol) in CH2Cl2 (5 mL) was added propionyl chloride (0.033 g, 0.35 mmol) and Et3N (0.049 mL, 0.35 mmol). The mixture was allowed to stir at room temp for 1 h, then was diluted with CH2Cl2 (40 mL). The resulting solution was sequentially washed with H2O (10 mL) and a saturated NaCl solution (10 mL), dried (Na2SO4), and concentrated under reduced pressure. The residue was purified by preparative TLC (40% EtOAc/hex) to give 2-(2-methyl-4-nitrophenylimino)-3-propanoyl-1,3-thiazolidine (0.036 g, 35%): FAB-MS m/z 294 ((M+H)+).

Workup

  1. washThe resulting solution was sequentially washed with H2O (10 mL)
  2. dry with materiala saturated NaCl solution (10 mL), dried (Na2SO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by preparative TLC (40% EtOAc/hex)

Sources & evidence

ORD record
ord-30ad3212d8ac49f9b4ed2ab816253146
Source dataset
uspto-grants-2002_03
Patent number
US06353006B1

Reaction notes

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