Dicyclohexylcarbodiimide → HCID 70607463, compound

HRID 261616Notes

Reaction equation

HRID 261616 reaction equation
[C:1]([NH:9][C@H:10]([C:24]([OH:26])=[O:25])[CH2:11][CH2:12][CH2:13][CH2:14][NH:15][C:16](=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(N=C=NC2CCCCC2)CCCCC1>O1CCOCC1>[C:16]([NH:15][CH2:14][CH2:13][CH2:12][CH2:11][C:10]1[C:24](=[O:25])[O:26][CH:1]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[N:9]=1)(=[O:23])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 10868DicyclohexylcarbodiimideHCID 12531082HCID 12531082, compound

Product 1

HCID 70607463HCID 70607463, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

N,N'-Dibenzoyl lysine (140.4 g, 0.36 mol) dissolved in dioxan (350 ml) was added over 45 min to dicyclohexylcarbodiimide (88.0 g, 0.43 mol) in dioxan (193 ml). After stirring for 2 hours the mixture was set aside overnight, filtered from dicyclohexylurea (88.1 g), concentrated to half volume and added to H2O. The precipitate was collected and recrystallised from methylal to give 4-(4-benzamidobutyl)-2-phenyl-5-oxazolone (104 g, 86%) m.p. 118°-122°.

Workup

  1. waitwas set aside overnight
  2. filtrationfiltered from dicyclohexylurea (88.1 g)
  3. concentrationconcentrated to half volume
  4. additionadded to H2O
  5. customThe precipitate was collected
  6. customrecrystallised from methylal

Sources & evidence

ORD record
ord-6faba5d6bc134a18bdb44af9023754e0
Source dataset
uspto-grants-1979_08
Patent number
US04166184

Reaction notes

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