Dicyclohexylcarbodiimide → HCID 19857803, compound

HRID 1902220Notes

Reaction equation

HRID 1902220 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[CH2:16]([CH:21]([CH:25]([OH:32])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[C:22]([OH:24])=[O:23])[CH2:17][CH2:18][CH2:19][CH3:20].O[N:34]1[C:38](=[O:39])[CH2:37][CH2:36][C:35]1=[O:40]>COCCOC>[CH2:16]([CH:21]([CH:25]([OH:32])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[C:22]([OH:24])=[O:23])[CH2:17][CH2:18][CH2:19][CH3:20].[C:35]1(=[O:40])[NH:34][C:38](=[O:39])[CH2:37][CH2:36]1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 19857780HCID 19857780, compound

Product 1

HCID 19857803HCID 19857803, compoundYield 104.2%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Dicyclohexylcarbodiimide (27 g) dissolved in 1,2-dimethoxyethane (300 cc) is added, in the course of 40 minutes, to a solution, kept at 0° C., of 2-n-pentyl-3-hydroxynonanoic acid (29.1 g) and N-hydroxysuccinimide (14.1 g) in 1,2-dimethoxyethane (300 cc). The reaction mixture is stirred at 0° C. for 3 hours and then kept at 4° C. for 21 hours. The precipitate formed is filtered off and washed twice with 1,2-dimethoxyethane (100 cc in total). The filtrate is concentrated to dryness under reduced pressure (20 mm Hg) at 50° C. The concentrate is taken up in a mixture of diisopropyl ether (300 cc) and acetic acid (3 cc). After standing for 2 hours at 20° C., the precipitate formed is filtered off and washed twice with diisopropyl ether (40 cc in total). The filtrate is concentrated to dryness under reduced pressure (20 mm Hg) at 50° C. Succinimide 2-n-pentyl-3-hydroxynonanoate (42.6 g) is thus obtained in the form of a yellow oil.

Workup

  1. additionis added, in the course of 40 minutes, to a solution
  2. waitkept at 4° C. for 21 hours
  3. customThe precipitate formed
  4. filtrationis filtered off
  5. washwashed twice with 1,2-dimethoxyethane (100 cc in total)
  6. concentrationThe filtrate is concentrated to dryness under reduced pressure (20 mm Hg) at 50° C
  7. additionThe concentrate is taken up in a mixture of diisopropyl ether (300 cc) and acetic acid (3 cc)
  8. waitAfter standing for 2 hours at 20° C.
  9. customthe precipitate formed
  10. filtrationis filtered off
  11. washwashed twice with diisopropyl ether (40 cc in total)
  12. concentrationThe filtrate is concentrated to dryness under reduced pressure (20 mm Hg) at 50° C

Sources & evidence

ORD record
ord-6cae515619a748c8921fbbabb2e435bf
Source dataset
uspto-grants-1982_12
Patent number
US04362716

Reaction notes

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