Carbamimidoylazanium Chloride → HCID 178422520, compound

HRID 733277Notes

Reaction equation

HRID 733277 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][C:20]([CH3:26])=[CH:21][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][C:20]([CH3:26])=[CH:21][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 69713690HCID 69713690, compound

Product 1

HCID 178422520HCID 178422520, compoundYield 59.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

N-[(2-Isobutyl-6-methyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetyl]guanidine is prepared as described in Example 1, starting with 2.52 g of potassium tert-butoxide, 2.58 g of guanidinium chloride and 1.3 g of ethyl (2-isobutyl-6-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 twice 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 0.81 g of N-[(2-isobutyl-6-methyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetyl]guanidine in the form of a white solid melting above 260° C. (Rf=0.28, thin layer chromatography on silica gel, eluent: dichloromethane/methanol (90/10 by volume)). (Analysis C16H22N4O2% calculated C, 63.56; H, 7.33; N, 18.53; O, 10.58%. found C, 63.40; H, 7.33; N, 18.37).

Workup

  1. customN-[(2-Isobutyl-6-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 twice 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-3305ace2140b4023bd3c3bc026202a88
Source dataset
uspto-grants-2009_09
Patent number
US07589117B2

Reaction notes

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