Carbamimidoylazanium Chloride → HCID 178422545, compound

HRID 733276Notes

Reaction equation

HRID 733276 reaction equation
CC(C)([O-])C.[K+].[Cl-].[NH2:8][C:9]([NH2:11])=[NH2+:10].[CH2:12]([N:16]1[C:24](=[O:25])[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([CH3:26])[CH:22]=2)[CH:17]1[CH2:27][C:28](OCC)=[O:29])[CH:13]([CH3:15])[CH3:14]>O>[CH2:12]([N:16]1[C:24](=[O:25])[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([CH3:26])[CH:22]=2)[CH:17]1[CH2:27][C:28]([NH:10][C:9]([NH2:11])=[NH:8])=[O:29])[CH:13]([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 5460839Carbamimidoylazanium ChlorideHCID 23665647Potassium tert-butoxideHCID 86591371HCID 86591371, compound

Product 1

HCID 178422545HCID 178422545, compoundYield 70.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

N-[(2-Isobutyl-5-methyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetyl]guanidine is prepared as described in Example 1, starting with 1.75 g of potassium tert-butoxide, 1.78 g of guanidinium chloride and 0.9 g of ethyl (2-isobutyl-5-methyl-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 40 hours and is then poured into 150 cm3 of water and extracted with 3 times 150 cm3 of ethyl acetate. The organic extracts are combined, washed with 3 times 50 cm3 of water, dried over magnesium sulphate, filtered and then concentrated to dryness under reduced pressure (2.7 kPa) at a temperature in the region of 40° C. The residue is taken up in diethyl ether and then filtered, giving 0.66 g of N-[(2-isobutyl-5-methyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetyl]guanidine in the form of a white solid melting at 266° C. (Analysis C16H22N4O2% calculated C, 63.56; H, 7.33; N, 18.53; O, 10.58%. found C, 63.57; H, 7.48; N, 18.50).

Workup

  1. customN-[(2-Isobutyl-5-methyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetyl]guanidine is prepared
  2. extractionextracted with 3 times 150 cm3 of ethyl acetate
  3. washwashed with 3 times 50 cm3 of water
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at a temperature in the region of 40° C
  7. filtrationfiltered

Sources & evidence

ORD record
ord-2dbba449fa434d9788c2413c171ec1da
Source dataset
uspto-grants-2009_09
Patent number
US07589117B2

Reaction notes

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