Toluene → HCID 131718739, compound

HRID 2380089Notes

Reaction equation

HRID 2380089 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([CH2:12][O:13][CH2:14][CH:15]([CH3:18])[CH2:16][CH3:17])[CH:9]=[CH:8][C:3]=1[O:4][CH2:5][CH2:6][NH2:7].C(N(CC)CC)C.C1(C(Cl)=[O:30])CC1.[C:32]1([CH3:38])[CH:37]=[CH:36][CH:35]=CC=1>>[Cl:1][C:2]1[CH:11]=[C:10]([CH2:12][O:13][CH2:14][CH:15]([CH3:18])[CH2:16][CH3:17])[CH:9]=[CH:8][C:3]=1[O:4][CH2:5][CH2:6][NH:7][C:38]([CH2:32][CH:37]1[CH2:36][CH2:35]1)=[O:30]

Participants

5

Reactant 4

HCID 1140Toluene2×HCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chlorideHCID 18956676HCID 18956676, compound

Product 1

HCID 131718739HCID 131718739, compound

Procedure

To a mixture of 181 g (0.667 mol) of 2-[2-chloro-4-(2-methylbutoxymethyl)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-(2-methylbutoxymethyl) 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-e8b4c53fd7b84636925dd20d1c8ad4da
Source dataset
uspto-grants-1994_11
Patent number
US05364966

Reaction notes

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