1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2,5-Dioxopyrrolidin-1-yl 4-bromo-2-chlorobenzoate

HRID 1352104Notes

Reaction equation

HRID 1352104 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([Cl:11])[CH:3]=1.O[N:13]1[C:17](=[O:18])[CH2:16][CH2:15][C:14]1=[O:19].CCN=C=NCCCN(C)C>O1CCCC1.CN(C)C=O>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][N:13]2[C:17](=[O:18])[CH2:16][CH2:15][C:14]2=[O:19])=[O:7])=[C:4]([Cl:11])[CH:3]=1

Participants

5

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 80170N-HydroxysuccinimideHCID 1088294-Bromo-2-chlorobenzoic acid

Product 1

HCID 159086832,5-Dioxopyrrolidin-1-yl 4-bromo-2-chlorobenzoateYield 92%

Reagents, catalysts & solvents 1

HCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Procedure

A solution of 4-bromo-2-chlorobenzoic acid (2.00 g, 8.5 mmol), N-hydroxysuccinimide (1.07 g, 9.3 mmol) and EDCI (1.79 g, 9.3 mmol) in tetrahydrofuran/N,N-dimethylformamide (3:1; 40 Ml) was stirred at room temperature for 18 h. The reaction was concentrated and water (50 Ml) was added. The mixture was extracted with ethyl acetate (3×50 Ml) and the combined organic layers were washed with brine, dried (Na2SO4), concentrated, and dried in vacuo to give 1-[(4-bromo-2-chlorobenzoyl)oxy]-2,5-pyrrolidinedione (2.59 g, 92%) as an off-white solid which was used directly in the next step without further purification.

Workup

  1. concentrationThe reaction was concentrated
  2. additionwater (50 Ml) was added
  3. extractionThe mixture was extracted with ethyl acetate (3×50 Ml)
  4. washthe combined organic layers were washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customdried in vacuo

Sources & evidence

ORD record
ord-f528edf8f9ec48b5abb8dd74c184948c
Source dataset
uspto-grants-2007_05
Patent number
US07217728B2

Reaction notes

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