Pyridine → 2-(m-Chlorophenyl)-3-isovaleroyl-5-ethyl-1,3-oxazolidine

HRID 621375Notes

Reaction equation

HRID 621375 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]2[NH:12][CH2:11][CH:10]([CH2:13][CH3:14])[O:9]2)[CH:5]=[CH:6][CH:7]=1.N1C=CC=CC=1.[C:21](Cl)(=[O:26])[CH2:22][CH:23]([CH3:25])[CH3:24]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]2[N:12]([C:21](=[O:26])[CH2:22][CH:23]([CH3:25])[CH3:24])[CH2:11][CH:10]([CH2:13][CH3:14])[O:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 66054Isovaleryl chlorideHCID 156146152-(m-Chlorophenyl)-5-ethyl-1,3-oxazolidine

Product 1

HCID 156146172-(m-Chlorophenyl)-3-isovaleroyl-5-ethyl-1,3-oxazolidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Four and two-tenths grams of 2-(m-chlorophenyl)-5-ethyl-1,3-oxazolidine was combined with 1.7 g of pyridine in 25 ml of methylene chloride and 2.4 g of isovaleroyl chloride was added dropwise with stirring and the mixture was stirred overnight. The mixture was washed with 50 ml of 5% NaOH and 200 ml of water, dried with MgSO4 and stripped under vacuum. The yield was 2.4 g, nD30 1.5490. The structure was confirmed by NMR and infrared spectroscopy.

Workup

  1. additionwas added dropwise
  2. stirringthe mixture was stirred overnight
  3. washThe mixture was washed with 50 ml of 5% NaOH and 200 ml of water
  4. dry with materialdried with MgSO4

Sources & evidence

ORD record
ord-e81a5fbc53ac44489b87356fdcb3957c
Source dataset
uspto-grants-1989_04
Patent number
US04824468

Reaction notes

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