1,1'-Carbonyldiimidazole → HCID 15053420, compound

HRID 1032104Notes

Reaction equation

HRID 1032104 reaction equation
Cl.[NH2:2][CH2:3][CH:4]1[CH2:6][CH2:5]1.[C:7]([N:14]1[CH:18]=[CH:17]N=[CH:15]1)(N1C=CN=C1)=[O:8].CO.C(Cl)Cl.C(O)(=O)C(O)=O.[F:30][C:31]([F:44])([F:43])[C:32]1[CH:33]=[C:34]([CH:40]=[CH:41][CH:42]=1)[O:35]C1CNC1>N1C=CC=CC=1.C(N(CC)CC)C>[CH:4]1([CH2:3][NH:2][C:7]([N:14]2[CH2:15][CH:17]([O:35][C:34]3[CH:40]=[CH:41][CH:42]=[C:32]([C:31]([F:30])([F:43])[F:44])[CH:33]=3)[CH2:18]2)=[O:8])[CH2:6][CH2:5]1

Participants

7

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 81671(Cyclopropylmethyl)ammonium chlorideHCID 19799580HCID 19799580, compoundHCID 21226129Dichloromethane methanol

Product 1

HCID 15053420HCID 15053420, compoundYield 103.4%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8471TriethylamineSolvent

Procedure

A solution of 2.6 g (0.024 mole) of (aminomethyl) cyclopropane hydrochloride in 50 ml of pyridine was stirred under a blanket of nitrogen while 3.9 g (0.024 mole) of 1,1'-carbonyldiimidazole was added. After stirring for 45 minutes, the TLC (5% methanol/methylene chloride on silica gel) showed no reaction; therefore, 2 ml of triethylamine was added. The reaction mixture after 10 minutes became cloudy and the TLC showed a new product. The reaction was treated with 6.2 g (0.02 mole) of 3-(3-(trifluoromethyl)phenoxy]azetidine oxalate. After stirring for 1 hr, a sample was removed, and upon dilution with water, a solid precipitated. The CI mass spectrum indicated it was product. After 2 days, the reaction was diluted with 5 volumes of water and the resulting precipitate collected by filtration to yield 6.5 g of pale yellow crystalline product. Recrystallization from ethanol/water produced white plate-like crystals which were dried at 82° C. for 3 hr in a drying pistol under vacuum; weight of the product was 5.8 g (92%), m.p. 132°-133° C.

Workup

  1. additionwas added
  2. customno reaction
  3. waitThe reaction mixture after 10 minutes became cloudy
  4. stirringAfter stirring for 1 hr
  5. customa sample was removed
  6. customupon dilution with water, a solid precipitated
  7. waitAfter 2 days
  8. additionthe reaction was diluted with 5 volumes of water
  9. filtrationthe resulting precipitate collected by filtration

Sources & evidence

ORD record
ord-6842c6a84f8446b289445d0b5e90551d
Source dataset
uspto-grants-1990_09
Patent number
US04956359

Reaction notes

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