Acetic Anhydride → Acetic acid N-hydroxysuccinimide ester

HRID 1165118Notes

Reaction equation

HRID 1165118 reaction equation
[OH:1][N:2]1[C:6](=[O:7])[CH2:5][CH2:4][C:3]1=[O:8].[C:9](OC(=O)C)(=[O:11])[CH3:10].C(N(CC)CC)C>O1CCCC1>[CH3:10][C:9]([O:1][N:2]1[C:6](=[O:7])[CH2:5][CH2:4][C:3]1=[O:8])=[O:11]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 80170N-Hydroxysuccinimide

Product 1

HCID 84460Acetic acid N-hydroxysuccinimide ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-Hydroxysuccinimide (17.33 g, 0.5 mol) was suspended in 120 ml tetrahydrofuran and cooled in an ice bath. Acetic anhydride (16 ml, 0.17 ml) and then triethylamine (22 ml, 0.16 mol) were added slowly. A solution formed, and then gradually a white precipitate appeared. After one half hour an equal volume of petroleum ether was added, and the crystalline product was collected. Yield 21.22 g (90%, mp 128°-130° C., lit. 15 mp 131°-132° C.). Analysis (C6H7NO4): calc. 45.87% C, 4.49% H, 8.91% N; found 45.86%, C, 4.31% H, 8.61% N.

Workup

  1. temperaturecooled in an ice bath
  2. customA solution formed
  3. customthe crystalline product was collected

Sources & evidence

ORD record
ord-175619cc98d54932a3666a48487c1ff6
Source dataset
uspto-grants-1990_03
Patent number
US04908322

Reaction notes

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