Triethylamine → HCID 66681362, compound

HRID 1171453Notes

Reaction equation

HRID 1171453 reaction equation
[C:1](Cl)(=[O:5])[C:2]([CH3:4])=[CH2:3].[OH:7][N:8]1[C:12](=[O:13])[CH2:11][CH2:10][C:9]1=[O:14].C(N(CC)CC)C>O1CCCC1>[C:1]([OH:5])(=[O:7])[C:2]([CH3:4])=[CH2:3].[OH:7][N:8]1[C:12](=[O:13])[CH2:11][CH2:10][C:9]1=[O:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13528Methacryloyl chlorideHCID 80170N-Hydroxysuccinimide

Product 1

HCID 66681362HCID 66681362, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Methacryloyl chloride (0.1 mol) in 25 ml of tetrahydrofuran was added dropwise with stirring and ice cooling to the solution of N-hydroxysuccinimide (0.1 mol) and triethylamine (0.1 mol) in 100 ml of tetrahydrofuran. After 1 hour of stirring at room temperature the precipitate is removed and filtrate is evaporated in vacuum. The residue was crystallized from methanol to give the product with 75% yield. M.P. 102-104° C.; M.p. lit. 103° C. (H.-G. Batz et al. Angew. Chem. Intern. Edit., 1972, v.11, N12, 1103-1104).

Workup

  1. stirringAfter 1 hour of stirring at room temperature the precipitate
  2. customis removed
  3. customfiltrate is evaporated in vacuum
  4. customThe residue was crystallized from methanol
  5. customto give the product with 75% yield
  6. customlit. 103° C.

Sources & evidence

ORD record
ord-3691b5743f4a4564ba2b368491ca58ed
Source dataset
uspto-grants-2010_11
Patent number
US07829644B2

Reaction notes

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