Triethylamine → HCID 11401002, compound

HRID 1955627Notes

Reaction equation

HRID 1955627 reaction equation
Cl.[CH:2]1([CH2:5][NH2:6])[CH2:4][CH2:3]1.[CH2:7](N(CC)CC)[CH3:8].[C:14]([N:21]1[CH:25]=[CH:24]N=C1)(N1C=CN=C1)=[O:15]>C(Cl)(Cl)Cl>[CH:2]1([CH2:5][NH:6][C:14]([NH:21][CH2:25][CH:24]2[CH2:8][CH2:7]2)=[O:15])[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 81671(Cyclopropylmethyl)ammonium chloride

Product 1

HCID 11401002HCID 11401002, compoundYield 59.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Cyclopropanemethylamine hydrochloride (Aldrich, 1.00 g, 9.30 mmol) and triethylamine (0.95 g, 9.39 mmol) were dissolved in chloroform (10 mL). 1,1'-Carbonyldiimidazole (Aldrich, 0.754 g, 4.65 mmol) was added and the resulting solution maintained at ~55° C. for 22 h. The chloroform solution was extracted with 1N hydrochloric acid (2×50 mL) and then with water (50 mL) and dried. Evaporation of the chloroform gave crude product (650 mg) which was recrystallized from toluene to give 1,3-bis(cyclopropylmethyl)urea as white crystals (462 mg, 59%), m.p. 127°-130° C.; 1H-NMR (DMSO-d6) consistent with structure.

Workup

  1. temperaturethe resulting solution maintained at ~55° C. for 22 h
  2. extractionThe chloroform solution was extracted with 1N hydrochloric acid (2×50 mL)
  3. dry with materialwith water (50 mL) and dried
  4. customEvaporation of the chloroform
  5. customgave crude product (650 mg) which
  6. customwas recrystallized from toluene

Sources & evidence

ORD record
ord-b83e3caf0aa04a61a4b73daa3af21c8b
Source dataset
uspto-grants-1998_07
Patent number
US05776940

Reaction notes

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