Carbamimidoylazanium Chloride → HCID 178456451, compound

HRID 1792904Notes

Reaction equation

HRID 1792904 reaction equation
CC(C)([O-])C.[K+].[Cl-].[NH2:8][C:9]([NH2:11])=[NH2+:10].[O:12]=[C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]([CH2:22][C:23](OCC)=[O:24])[N:14]1[CH2:28][CH2:29][CH3:30]>O>[O:12]=[C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]([CH2:22][C:23]([NH:10][C:9]([NH2:11])=[NH:8])=[O:24])[N:14]1[CH2:28][CH2:29][CH3:30]

Participants

5

Reactant 3

HCID 5460839Carbamimidoylazanium ChlorideHCID 23665647Potassium tert-butoxideHCID 85891564ethyl (3-oxo-2-propyl-2,3-dihydro-1H-isoindol-1-yl)acetate

Product 1

HCID 178456451HCID 178456451, compoundYield 31.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

N-[(3-Oxo-2-propyl-2,3-dihydro-1H-isoindol-1-yl)acetyl]guanidine is prepared as described in Example 1, starting with 3.9 g of potassium tert-butoxide, 3.3 g of guanidinium chloride and 1.8 g of ethyl (3-oxo-2-propyl-2,3-dihydro-1H-isoindol1-yl)acetate. The reaction mixture is stirred at a temperature in the region of 20° C. for 1 hour, 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. 0.6 g of N-[(3-oxo-2-propyl-2,3-dihydro-1H-isoindol-1-yl)acetyl]-guanidine is thus obtained in the form of a pale yellow cottony solid melting at 229° C. Mass spectrum EI: m/e 274 (M+), m/e 187, m/e 86 (base peak).

Workup

  1. customN-[(3-Oxo-2-propyl-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-b2dd0a2274da4fd9a4bbd7aca7dd0685
Source dataset
uspto-grants-2006_07
Patent number
US07078428B2

Reaction notes

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