Carbamimidoylazanium Chloride → HCID 178462846, compound

HRID 733215Notes

Reaction equation

HRID 733215 reaction equation
CC(C)([O-])C.[K+].[Cl-].[NH2:8][C:9]([NH2:11])=[NH2+:10].[CH2:12]([N:14]1[C:22](=[O:23])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]1[CH2:24][C:25](OCC)=[O:26])[CH3:13]>O>[CH2:12]([N:14]1[C:22](=[O:23])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]1[CH2:24][C:25]([NH:10][C:9]([NH2:11])=[NH:8])=[O:26])[CH3:13]

Participants

5

Reactant 3

HCID 5460839Carbamimidoylazanium ChlorideHCID 23665647Potassium tert-butoxideHCID 86591360ethyl (2-ethyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetate

Product 1

HCID 178462846HCID 178462846, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

N-[(2-Ethyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetyl]guanidine is prepared as described in Example 1, starting with 4.3 g of potassium tert-butoxide, 3.7 g of guanidinium chloride and 1.9 g of ethyl (2-ethyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetate. The reaction mixture is stirred at a temperature in the region of 20° C. for 20 hours, followed by addition of 60 cm3 of water. The aqueous phase is extracted with 3 times 50 cm3 of ethyl acetate and is then concentrated to dryness under reduced pressure (0.6 kPa) at a temperature in the region of 45° C. The residue is taken up in water, triturated and filtered. The solid is taken up in methanol and the solvent is then evaporated to dryness under reduced pressure (0.6 kPa) at a temperature in the region of 45° C. 0.56 g of N-[(2-ethyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetyl]-guanidine is thus obtained in the form of an off-white solid melting at 223° C. Mass spectrum EI: m/e 260 (M+), m/e 173, m/e 160, m/e 132.

Workup

  1. customN-[(2-Ethyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetyl]guanidine is prepared
  2. extractionThe aqueous phase is extracted with 3 times 50 cm3 of ethyl acetate
  3. concentrationis then concentrated to dryness under reduced pressure (0.6 kPa) at a temperature in the region of 45° C
  4. customtriturated
  5. filtrationfiltered
  6. customthe solvent is then evaporated to dryness under reduced pressure (0.6 kPa) at a temperature in the region of 45° C

Sources & evidence

ORD record
ord-4dc12b006aff4a4b9c25c9da79083658
Source dataset
uspto-grants-2009_09
Patent number
US07589117B2

Reaction notes

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