Dicyclohexylcarbodiimide → 1-[[4-(Azidomethyl)-2-chlorobenzoyl]oxy]-2,5-pyrrolidinedione

HRID 2270867Notes

Reaction equation

HRID 2270867 reaction equation
[N:1]([CH2:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[C:7]([Cl:14])[CH:6]=1)=[N+:2]=[N-:3].O[N:16]1[C:20](=[O:21])[CH2:19][CH2:18][C:17]1=[O:22].C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1>[N:1]([CH2:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([O:11][N:16]2[C:20](=[O:21])[CH2:19][CH2:18][C:17]2=[O:22])=[O:10])=[C:7]([Cl:14])[CH:6]=1)=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 226614994-(Azidomethyl)-2-chlorobenzoic acid

Product 1

HCID 226614281-[[4-(Azidomethyl)-2-chlorobenzoyl]oxy]-2,5-pyrrolidinedioneYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-(azidomethyl)-2-chlorobenzoic acid (6.82 g, 32.2 mmol), N-hydroxysuccinimide (5.19 g, 45.1 mmol) and dicyclohexylcarbodiimide (9.31 g, 45.1 mmol) in tetrahydrofuran (250 mL) was stirred overnight at room temperature. The dicyclohexylurea (7.70 g, 76%) was filtered off and discarded. Silica gel was added, the solvent was evaporated and the residue was chromatographed (40-60% ethyl acetate/hexanes) to give 1-[[4-(azidomethyl)-2-chlorobenzoyl]oxy]-2,5-pyrrolidinedione (9.64 g, 97%) as a white solid.

Workup

  1. filtrationThe dicyclohexylurea (7.70 g, 76%) was filtered off
  2. additionSilica gel was added
  3. customthe solvent was evaporated
  4. customthe residue was chromatographed (40-60% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-3d8d09159c8942be89d22edd03d623aa
Source dataset
uspto-grants-2001_12
Patent number
US06331640B1

Reaction notes

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