Sodium → HCID 178448654, compound

HRID 1792921Notes

Reaction equation

HRID 1792921 reaction equation
[Na].[Cl-:2].[NH2:3][C:4]([NH2:6])=[NH2+:5].[Cl:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[CH:13]([CH2:17][C:18](OCC)=[O:19])[N:12]([CH2:23][CH:24]([CH3:26])[CH3:25])[C:11]2=[O:27]>C(O)C>[Cl:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[CH:13]([CH2:17][C:18]([NH:5][C:4]([NH2:6])=[NH:3])=[O:19])[N:12]([CH2:23][CH:24]([CH3:25])[CH3:26])[C:11]2=[O:27].[Cl:2][C:16]1[CH:15]=[C:14]2[C:10]([C:11](=[O:27])[N:12]([CH2:23][CH:24]([CH3:26])[CH3:25])[CH:13]2[CH2:17][C:18]([NH:5][C:4]([NH2:6])=[NH:3])=[O:19])=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 5360545SodiumHCID 5460839Carbamimidoylazanium ChlorideHCID 86591363HCID 86591363, compound

Product 2

HCID 178448654HCID 178448654, compoundHCID 178448657HCID 178448657, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
20 °C

Procedure

N-[(5-Chloro-2-isobutyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetyl]guanidine and N-[(6chloro-2-isobutyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetyl]guanidine are prepared as described in Example 9, starting with 20 cm3 of absolute ethanol, 0.35 g of sodium, 1.46 g of guanidinium chloride and 3.1 g of ethyl (5-chloro-2-isobutyl-3-oxo-2,3dihydro-1-H-isoindol-1-yl)acetate and ethyl (6-chloro-2-isobutyl-3-oxo-2,3-dihydro-1isoindol-1-yl)acetate in 15 cm3 of absolute ethanol. The reaction mixture is stirred at a temperature in the region of 20° C. for 18 hours and is then concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C. The residue is taken up in a mixture of 15 cm3 of water and 45 cm3 of diethyl ether and then stirred at a temperature in the region of 0° C. for 4 hours. The precipitate obtained is filtered off, washed with twice 20 cm3 of ice-cold water and then dried in a desiccator under reduced pressure (2 kPa) at a temperature in the region of 20° C. 1 g of N-[(5-chloro-2isobutyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetyl]quanidine and N-[(6-chloro-2-isobutyl-3-oxo-2,3-dibydro-1H-isoindol-1-yl)acetyl]guanidine is thus obtained in the form of a white powder. (Analysis: C15 H19 Cl N4 O2, % calculated C: 55.81, H: 5.93, Cl: 10.98, N: 17.36, O: 9.91% found C: 55.67, H: 6.18, Cl: 11.32, N: 17.05). Mass spectrum: DCI: m/e 323 (M+H)+.

Workup

  1. concentrationis then concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C
  2. additionThe residue is taken up in a mixture of 15 cm3 of water and 45 cm3 of diethyl ether
  3. stirringstirred at a temperature in the region of 0° C. for 4 hours
  4. customThe precipitate obtained
  5. filtrationis filtered off
  6. washwashed with twice 20 cm3 of ice-cold water
  7. customdried in a desiccator under reduced pressure (2 kPa) at a temperature in the region of 20° C

Sources & evidence

ORD record
ord-59ecbc226b2140e2806ae1c04f1b3579
Source dataset
uspto-grants-2006_07
Patent number
US07078428B2

Reaction notes

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