Sodium → HCID 178448654, compound

HRID 733231Notes

Reaction equation

HRID 733231 reaction equation
[Na].[Cl-].[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].[Cl:28][C:29]1[CH:37]=[C:36]2[C:32]([C:33](=[O:48])[N:34]([CH2:44][CH:45]([CH3:47])[CH3:46])[CH:35]2[CH2:38][C:39](OCC)=[O:40])=[CH:31][CH:30]=1>C(O)C>[Cl:28][C:29]1[CH:37]=[C:36]2[C:32]([C:33](=[O:48])[N:34]([CH2:44][CH:45]([CH3:46])[CH3:47])[CH:35]2[CH2:38][C:39]([NH:5][C:4]([NH2:6])=[NH:3])=[O:40])=[CH:31][CH:30]=1.[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]

Participants

7

Reactant 4

HCID 5360545SodiumHCID 5460839Carbamimidoylazanium ChlorideHCID 69715450HCID 69715450, compoundHCID 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-[(6-chloro-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-2,3-dihydro-1H-isoindol-1-yl)acetate and ethyl (6-chloro-2-isobutyl-3-oxo-2,3-dihydro-1H-isoindol-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-2-isobutyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetyl]guanidine and N-[(6-chloro-2-isobutyl-3-oxo-2,3-dihydro-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-94cb916d8c824a968208b121ae7a8522
Source dataset
uspto-grants-2009_09
Patent number
US07589117B2

Reaction notes

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