Potassium Iodide → HCID 22170541, compound

HRID 1822886Notes

Reaction equation

HRID 1822886 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH2:12][C:13]([NH:15][C:16]2[S:17][C:18]([CH:21]([CH3:23])[CH3:22])=[CH:19][N:20]=2)=[O:14])[CH:9]=[CH:10][CH:11]=1.[NH:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1.[I-].[K+]>CN(C)C=O>[CH:21]([C:18]1[S:17][C:16]([NH:15][C:13](=[O:14])[CH2:12][C:8]2[CH:9]=[CH:10][CH:11]=[C:6]([O:5][CH2:4][CH2:3][CH2:2][N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)[CH:7]=2)=[N:20][CH:19]=1)([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 8083MorpholineHCID 22170841HCID 22170841, compound

Product 1

HCID 22170541HCID 22170541, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-[3-(3-chloropropoxy)phenyl]-N-(5-isopropyl-1,3-thiazol-2-yl)acetamide (1.00 g, 2.8 mmoles), morpholine (1.24 ml, 14.2 mmoles), potassium iodide (0.24 g, 1.4 mmoles) in anhydrous dimethylformamide (3.5 ml) was heated at 100° C. for 6 hours. The solution was acidified and extracted with ether to eliminate unreacted products; then the solution was basified and extracted with ether. The solvent was evaporated to dryness to give the product as an oily semisolid which was purified by flash chromatography with dichloromethane:methanol (97:3) as eluent (1.0 g, 87% yield)

Workup

  1. extractionextracted with ether
  2. extractionextracted with ether
  3. customThe solvent was evaporated to dryness

Sources & evidence

ORD record
ord-8290e87c12534f90844d32dca1941be9
Source dataset
uspto-grants-2006_05
Patent number
US07037929B1

Reaction notes

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