N-Hydroxysuccinimide → 2,5-Dioxopyrrolidin-1-yl 4-bromo-2-chlorobenzoate

HRID 393106Notes

Reaction equation

HRID 393106 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.Cl>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 80170N-HydroxysuccinimideHCID 1088294-Bromo-2-chlorobenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

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 EDCl (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-6486ed10dce847f9bce722c2ef87d4f7
Source dataset
uspto-grants-2004_10
Patent number
US06803384B2

Reaction notes

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