Triethylamine → HCID 21903111, compound

HRID 1165119Notes

Reaction equation

HRID 1165119 reaction equation
ON1C(=O)CCC1=O.[C:9]([O:13]C(=O)CC)(=[O:12])[CH2:10][CH3:11].[CH2:18]([N:20]([CH2:23][CH3:24])[CH2:21][CH3:22])[CH3:19]>C(OCC)(=O)C>[C:9]([O-:13])(=[O:12])[CH2:10][CH3:11].[CH2:18]([NH+:20]([CH2:23][CH3:24])[CH2:21][CH3:22])[CH3:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31263Propionic anhydrideHCID 80170N-Hydroxysuccinimide

Product 1

HCID 21903111HCID 21903111, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

N-hydroxysuccinimide (32.06 g) was suspended in ethyl acetate (150 ml). Propionic anhydride (37 ml) and triethylamine (39 ml) were added alternately in small portions. A solution formed and the vessel became warm as the reaction progressed. After cooling to room temperature, several milliliters of saturated saline were added, resulting in the precipitation of a thick crystalline mass (triethylammonium propionate). The solid was filtered and washed with ethyl acetate. The combined filtrate was washed with saturated saline (3×) and water (1×). Evaporation of the organic layer left a residue of oil, which crystallized upon scratching with a glass rod and trituration with petroleum ether to give 45.36 g of product (95.2% yield). Mp. 44°-46° C., analysis (C7H9NO4); calc. 49.62% C, 5.30% H, 8.18% N; found 49.29% C, 5.20% H, 8.19% N.

Workup

  1. customA solution formed
  2. temperaturethe vessel became warm as the reaction
  3. additionseveral milliliters of saturated saline were added

Sources & evidence

ORD record
ord-d7e6df5660ef4b34b84a830d1a344103
Source dataset
uspto-grants-1990_03
Patent number
US04908322

Reaction notes

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