Sodium Iodide → HCID 11514810, compound

HRID 1801488Notes

Reaction equation

HRID 1801488 reaction equation
[NH2:1][C:2]1[CH:9]=[C:8]([O:10][CH2:11][CH2:12][CH2:13]Cl)[C:7]([O:15][CH3:16])=[CH:6][C:3]=1[C:4]#[N:5].[NH:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1.[I-].[Na+]>>[NH2:1][C:2]1[CH:9]=[C:8]([O:10][CH2:11][CH2:12][CH2:13][N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[C:7]([O:15][CH3:16])=[CH:6][C:3]=1[C:4]#[N:5]

Participants

4

Reactant 3

HCID 5238Sodium IodideHCID 8083MorpholineHCID 534010272-Amino-4-(3-chloropropoxy)-5-methoxybenzonitrile

Product 1

HCID 11514810HCID 11514810, compound

Procedure

A mixture of 2-amino-4-chloropropoxy-5-methoxy-benzonitrile (1.000 g, 4.12 mmol), morpholine (1.0 mL) and catalytic amount of sodium iodide were added into a round bottom flask. The solution was stirred and heated under reflux for 2 h. After reaction, extracted the solution with dichloromethane and water, and then combined the organic phases. After evaporating most of the solvent, equivalent amount of hydrochloric acid ether was added into the solution, and filtered to yield 1.100 g of white solid product with a recovery rate of 91%.

Workup

  1. additionwere added into a round bottom flask
  2. temperatureheated
  3. temperatureunder reflux for 2 h
  4. customAfter reaction
  5. extractionextracted the solution with dichloromethane and water
  6. customAfter evaporating most of the solvent, equivalent amount of hydrochloric acid ether
  7. additionwas added into the solution
  8. filtrationfiltered

Sources & evidence

ORD record
ord-ef633660b14c4061a6222317d1f19bf8
Source dataset
uspto-grants-2013_01
Patent number
US08349835B2

Reaction notes

Loading…