Toluene → HCID 131718738, compound

HRID 2380088Notes

Reaction equation

HRID 2380088 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([CH2:12][O:13][CH2:14][CH2:15][CH3:16])[CH:9]=[CH:8][C:3]=1[O:4][CH2:5][CH2:6][NH2:7].C(N(CC)CC)C.C1(C(Cl)=[O:28])CC1.[C:30]1([CH3:36])[CH:35]=[CH:34][CH:33]=CC=1>>[Cl:1][C:2]1[CH:11]=[C:10]([CH2:12][O:13][CH2:14][CH2:15][CH3:16])[CH:9]=[CH:8][C:3]=1[O:4][CH2:5][CH2:6][NH:7][C:36]([CH2:30][CH:35]1[CH2:34][CH2:33]1)=[O:28]

Participants

5

Reactant 4

HCID 1140Toluene2×HCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chlorideHCID 18956682HCID 18956682, compound

Product 1

HCID 131718738HCID 131718738, compound

Procedure

To a mixture of 162 g (0.667 mol) of 2-(2-chloro-4-propoxymethylphenoxy)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-propoxymethylphenoxy)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-d0283a7938054fd6b4f883d7990bd748
Source dataset
uspto-grants-1994_11
Patent number
US05364966

Reaction notes

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