Hydrochloric Acid → HCID 178481324, compound
Reaction equation
[Cl-].[NH2:2][C:3]([NH2:5])=[NH2+:4].CC(C)([O-])C.[K+].[CH3:12][N:13]1[C:21](=[O:22])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]1[CH2:23][C:24](OCC)=[O:25].Cl>CN(C)C=O.O>[CH3:12][N:13]1[C:21](=[O:22])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]1[CH2:23][C:24]([NH:4][C:3]([NH2:5])=[NH:2])=[O:25]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 20 °C
Procedure
4.3 g of guanidinium chloride are added to a suspension of 5.2 g of potassium tert-butoxide in 100 cm3 of dimethylformamide. The reaction mixture is stirred under an inert atmosphere at a temperature in the region of 20° C. for 1 hour, followed by addition of a solution of 2 g of ethyl (2-methyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetate in 20 cm3 of dimethylformamide. The reaction mixture is stirred at a temperature in the region of 20° C. for 16 hours, followed by addition of 100 cm3 of water. The pH is adjusted to 8 by adding 50 cm3 of 1N hydrochloric acid, and the mixture is concentrated under reduced pressure (0.6 kPa) at a temperature in the region of 30° C. The evaporation residue is taken up in water and then filtered. 0.35 g of N-[(2-methyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetyl]guanidine is thus obtained in the form of an off-white solid melting at 214° C. Mass spectrum EI: m/e 246 (M+), m/e 159 (base peak), m/e 146.
Workup
- stirringThe reaction mixture is stirred at a temperature in the region of 20° C. for 16 hours
- concentrationthe mixture is concentrated under reduced pressure (0.6 kPa) at a temperature in the region of 30° C
- filtrationfiltered
Sources & evidence
- ORD record
- ord-cdc427f4bb4d41d4a10b95f58a21aaa2
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07589117B2
Reaction notes
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