Pyridine → HCID 11042130, compound

HRID 2200065Notes

Reaction equation

HRID 2200065 reaction equation
[OH:1][N:2]1[C:6](=[O:7])[CH2:5][CH2:4][C:3]1=[O:8].N1C=CC=CC=1.[C:15]([O:18][CH2:19][C:20](Cl)=[O:21])(=[O:17])[CH3:16]>C(Cl)Cl>[C:15]([O:18][CH2:19][C:20]([O:1][N:2]1[C:6](=[O:7])[CH2:5][CH2:4][C:3]1=[O:8])=[O:21])(=[O:17])[CH3:16]

Participants

5

Reactant 3

HCID 1049PyridineHCID 26297Acetoxyacetyl chlorideHCID 80170N-Hydroxysuccinimide

Product 1

HCID 11042130HCID 11042130, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 3-neck round-bottom flask equipped with a mechanical stirrer, thermocouple and addition funnel with nitrogen inlet was charged with N-hydroxysuccinimide (commercially available from Sigma-Aldrich, St. Louis, Mo.) (211 g, 1.83 mol) and DCM (2.25 L) at room temperature, resulting in a suspension. Pyridine (178 mL, 2.2 mol) was added in one portion with no change in the internal temperature. A solution of acetoxyacetyl chloride (commercially available from Sigma-Aldrich, St. Louis, Mo.) (197 mL, 1.83 mol) in DCM (225 mL) was added dropwise over 60 minutes and the temperature rose to 35° C. Stirring was continued at room temperature for 2.5 hours. The reaction mixture was washed with water (1×1 L), 1N HCl (2×1 L) and brine (1×1 L). The organic layer was concentrated under vacuum and azeotroped with toluene (1×1 L) to obtain the product as a white solid (367 g, 93%). 1H NMR (400 MHz, CDCl3) δ 4.96 (2H, s), 2.86 (4H, s), 2.19 (3H, s) ppm; LCMS m/z: 238 (M+Na).

Workup

  1. customA 3-neck round-bottom flask equipped with a mechanical stirrer
  2. additionthermocouple and addition funnel with nitrogen inlet
  3. customrose to 35° C
  4. washThe reaction mixture was washed with water (1×1 L), 1N HCl (2×1 L) and brine (1×1 L)
  5. concentrationThe organic layer was concentrated under vacuum
  6. customazeotroped with toluene (1×1 L)

Sources & evidence

ORD record
ord-1fa1e353064647b8af9bf239b726ab52
Source dataset
uspto-grants-2016_06
Patent number
US09359355B2

Reaction notes

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