Pyridine → HCID 15614620, compound

HRID 621378Notes

Reaction equation

HRID 621378 reaction equation
[C:1](Cl)(=[O:6])[CH2:2][CH:3]([CH3:5])[CH3:4].[C:8]([C:10]1[CH:11]=[C:12]([CH:16]2[NH:20][CH2:19][CH:18]([CH2:21][CH3:22])[O:17]2)[CH:13]=[CH:14][CH:15]=1)#[N:9].N1C=CC=CC=1>C(Cl)Cl>[C:8]([C:10]1[CH:11]=[C:12]([CH:16]2[N:20]([C:1](=[O:6])[CH2:2][CH:3]([CH3:5])[CH3:4])[CH2:19][CH:18]([CH2:21][CH3:22])[O:17]2)[CH:13]=[CH:14][CH:15]=1)#[N:9]

Participants

5

Reactant 3

HCID 1049PyridineHCID 66054Isovaleryl chlorideHCID 21242489HCID 21242489, compound

Product 1

HCID 15614620HCID 15614620, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Two and five-tenths grams of isovaleroyl chloride in 10 ml of methylene chloride was added dropwise to 6.5 g of 2-(m-cyanophenyl)-5-ethyl-1,3-oxazolidine in 25 ml of methylene chloride containing 1.9 g of pyridine. The mixture was allowed to stir overnight, washed with 50 ml of 5% NaOH and 200 ml of water, dried over anhydrous MgSO4 and stripped on the rotary evaporator. The yield was 3.7 g, nD30 1.5455. The structure was confirmed by NMR and infrared spectroscopy.

Workup

  1. washwashed with 50 ml of 5% NaOH and 200 ml of water
  2. dry with materialdried over anhydrous MgSO4
  3. customstripped on the rotary evaporator

Sources & evidence

ORD record
ord-71e63ee5ced94f6c97dea9e9728b7e49
Source dataset
uspto-grants-1989_04
Patent number
US04824468

Reaction notes

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