Benzamidine → HCID 70531705, compound

HRID 2287140Notes

Reaction equation

HRID 2287140 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([N:7]=[C:8](Cl)[Cl:9])=[CH:3][CH:2]=1.[NH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1.C(N(CC)CC)C.[C:24]([NH2:32])(=[NH:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CCOCC.O1CCCC1>[ClH:9].[NH2:32][C:24](=[N:31][C:8]([N:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1)=[N:7][C:4]1[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

7

Reactant 4

HCID 2332BenzamidineHCID 8083MorpholineHCID 8471TriethylamineHCID 12145Phenylimidocarbonyl chloride

Product 1

HCID 70531705HCID 70531705, compoundYield 32.8%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To 3.48 g (0.02 mol) of phenylisocyanide dichloride in 25 ml of anhydrous ether at 0° C. under a nitrogen atmosphere was added 1.74 g (0.02 mol) of morpholine and 2.02 g (0.02 mol) of triethylamine in 20 ml of ether dropwise. The mixture was stirred for 22 hours and filtered to remove the precipitated triethylamine hydrochloride. To a solution of 4.8 g (0.04 mol) of benzamidine in 15 ml of anhydrous tetrahydrofuran at 0° C. was added the above filtrate dropwise. The mixture was stirred for 22 hours at ambient temperature. The precipitated crude product was collected, washed with anhydrous ether, chromatographed on 150 g of silica gel using 1:6 methanol-dichloromethane and recrystallized from methanol-ether to afford 2.26 g (32%) of N-(1-amino-1-phenylmethylene)-N'-phenyl-4-morpholinecarboximidamide hydrochloride, mp 247°-248° C.

Workup

  1. filtrationfiltered
  2. customto remove the precipitated triethylamine hydrochloride
  3. stirringThe mixture was stirred for 22 hours at ambient temperature
  4. customThe precipitated crude product
  5. customwas collected
  6. washwashed with anhydrous ether
  7. customchromatographed on 150 g of silica gel using 1:6 methanol-dichloromethane
  8. customrecrystallized from methanol-ether

Sources & evidence

ORD record
ord-eae65c1467564e26a376ab3f6d62f285
Source dataset
uspto-grants-1981_05
Patent number
US04269837

Reaction notes

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