Toluene → HCID 131718737, compound

HRID 1708227Notes

Reaction equation

HRID 1708227 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([O:12][C:13]2[CH:14]=[C:15]([CH3:19])[CH:16]=[CH:17][CH:18]=2)[CH:9]=[CH:8][C:3]=1[O:4][CH2:5][CH2:6][NH2:7].C(N(CC)CC)C.C1(C(Cl)=[O:31])CC1.[C:33]1([CH3:39])[CH:38]=[CH:37][CH:36]=CC=1>>[Cl:1][C:2]1[CH:11]=[C:10]([O:12][C:13]2[CH:14]=[C:15]([CH3:19])[CH:16]=[CH:17][CH:18]=2)[CH:9]=[CH:8][C:3]=1[O:4][CH2:5][CH2:6][NH:7][C:39]([CH2:33][CH:38]1[CH2:37][CH2:36]1)=[O:31]

Participants

5

Reactant 4

HCID 1140Toluene2×HCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chlorideHCID 18956673HCID 18956673, compound

Product 1

HCID 131718737HCID 131718737, compound

Procedure

To a mixture of 185 g (0.667 mol) of 2-[2-chloro-4-(3-tolyloxy)phenoxy]ethylamine, 81 g (0.80 mol) of triethylamine and 8 liter of toluene, there is added dropwise a solution of 70 g (0.67 mol) of cyclopropane carbonyl chloride in 2 liter of toluene with stirring at a temperature of from 5° C. to 10° C. After 2 hours, the reaction mixture is stirred at a room temperature for 15 hours. After the reaction is completed, the resultant mixture is washed twice with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue is subjected to silica gel chromatography to give N-{2-[2-chloro-4-(3-tolyloxy)phenoxy]ethyl}-cyclopropane carboxyamide.

Workup

  1. stirringthe reaction mixture is stirred at a room temperature for 15 hours
  2. washthe resultant mixture is washed twice with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e3ac799862824237914304723b730859
Source dataset
uspto-grants-1994_10
Patent number
US05356930

Reaction notes

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