Sodium → HCID 178448651, compound

HRID 733230Notes

Reaction equation

HRID 733230 reaction equation
[Na].[Cl-].[NH2:3][C:4]([NH2:6])=[NH2+:5].[C:7]([C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[CH:16]([CH2:20][C:21](OCC)=[O:22])[N:15]([CH2:26][CH:27]([CH3:29])[CH3:28])[C:14]2=[O:30])([CH3:10])([CH3:9])[CH3:8]>C(O)C>[C:7]([C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[CH:16]([CH2:20][C:21]([NH:5][C:4]([NH2:6])=[NH:3])=[O:22])[N:15]([CH2:26][CH:27]([CH3:28])[CH3:29])[C:14]2=[O:30])([CH3:10])([CH3:9])[CH3:8]

Participants

5

Reactant 3

HCID 5360545SodiumHCID 5460839Carbamimidoylazanium ChlorideHCID 86591362ethyl (5-tert-butyl-2-isobutyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetate

Product 1

HCID 178448651HCID 178448651, compoundYield 58.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
20 °C

Procedure

N-[(5-tert-Butyl-2-isobutyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetyl]guanidine is prepared as described in Example 9, starting with 10 cm3 of absolute ethanol, 0.19 g of sodium, 0.80 g of guanidinium chloride and 1.81 g of ethyl (5-tert-butyl-2-isobutyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetate in 10 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 10 cm3 of water and 30 cm3 of diethyl ether and then stirred at a temperature in the region of 0° C. for 1 hour. The precipitate obtained is filtered off, washed with twice 10 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. 1.1 g of N-[(5-tert-butyl-2-isobutyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetyl]guanidine are thus obtained in the form of a white powder melting at 262-263° C. Ethyl (5-tert-butyl-2-isobutyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetate is described in Example 10. (Analysis: C19 H28 N4 O2; % calculated C, 66.25; H, 8.19; N, 16.27; O, 9.29%. found C, 66.13; H, 8.50; N, 16.12).

Workup

  1. customN-[(5-tert-Butyl-2-isobutyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetyl]guanidine is prepared
  2. concentrationis then concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C
  3. additionThe residue is taken up in a mixture of 10 cm3 of water and 30 cm3 of diethyl ether
  4. stirringstirred at a temperature in the region of 0° C. for 1 hour
  5. customThe precipitate obtained
  6. filtrationis filtered off
  7. washwashed with twice 10 cm3 of ice-cold water
  8. customdried in a desiccator under reduced pressure (2 kPa) at a temperature in the region of 20° C

Sources & evidence

ORD record
ord-8640f2cbe1e8431a9e42f886bbdf74ef
Source dataset
uspto-grants-2009_09
Patent number
US07589117B2

Reaction notes

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