N,N'-Dicyclohexylurea → 1-[(3-Hydroxybenzoyl)oxy]pyrrolidine-2,5-dione

HRID 482205Notes

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]

Participants

7

Reactant 4

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

Product 1

HCID 203108021-[(3-Hydroxybenzoyl)oxy]pyrrolidine-2,5-dione

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 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
Patent number
US05795729

Reaction notes

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