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N,N'-Dicyclohexylurea → 2,5-Pyrrolidinedione, 1-[(3-hydroxybenzoyl)oxy]-

HRID 482205
Notes
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Reaction equation

HRID 482205 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[OH:16][C:17]1[CH:18]=[C:19]([CH:23]=[CH:24][CH:25]=1)[C:20]([OH:22])=[O:21].O[N:27]1[C:31](=[O:32])[CH2:30][CH2:29][C:28]1=[O:33].C(NC1CCCCC1)(NC1CCCCC1)=O>C(OCC)(=O)C.C(O)(=O)C>[OH:16][C:17]1[CH:18]=[C:19]([CH:23]=[CH:24][CH:25]=1)[C:20]([O:22][N:27]1[C:31](=[O:32])[CH2:30][CH2:29][C:28]1=[O:33])=[O:21]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 4277N,N'-DicyclohexylureaHCID 74203-Hydroxybenzoic AcidHCID 10868DicyclohexylcarbodiimideHCID 80170N-Hydroxysuccinimide

Product 1

HCID 203108022,5-Pyrrolidinedione, 1-[(3-hydroxybenzoyl)oxy]-

Reagents, catalysts & solvents 2

HCID 176
Acetic Acid
Solvent
HCID 8857Ethyl AcetateSolvent

Procedure

As illustrated in Scheme 1 below, 1,3-dicyclohexylcarbodiimide (82 mg, 0.40 mmol) was added to a solution of 3-hydroxybenzoic acid (50 mg, 0.36 mmol) and N-hydroxysuccinimide (46 mg, 0.40 mmol) in ethyl acetate (1 mL). After 1 minute, crystals of dicyclohexylurea appeared. The next day, acetic acid (20 μL) was added. The mixture was filtered through glass wool, washed with dilute HCl (1N) and dried over Na2SO4. The solution was concentrated to a white solid. Thin layer chromatography on silica gel with 1:1 ethyl acetate:hexane showed complete conversion of the starting acid to a fluorescent, lower rf product. ##STR2##

Workup

  1. filtrationThe mixture was filtered through glass wool
  2. washwashed with dilute HCl (1N)
  3. dry with materialdried over Na2SO4
  4. concentrationThe solution was concentrated to a white solid

Sources & evidence

ORD record
ord-53b8ef1ea9a54fbb8297972007115b51
Source dataset
uspto-grants-1998_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05795729

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes