Sodium Azide → HCID 86668988, compound

HRID 2366171Notes

Reaction equation

HRID 2366171 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[Cl:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Cl:12])[C:7]=1[C:13]1[S:14][CH:15]=[C:16](/[CH:18]=[CH:19]/[C:20](Cl)=[O:21])[N:17]=1>O.CC(C)=O.O1CCOCC1>[Cl:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Cl:12])[C:7]=1[C:13]1[S:14][CH:15]=[C:16](/[CH:18]=[CH:19]/[C:20]([N:1]=[N+:2]=[N-:3])=[O:21])[N:17]=1

Participants

6

Reactant 2

HCID 33557Sodium AzideHCID 86668989HCID 86668989, compound

Product 1

HCID 86668988HCID 86668988, compoundYield 98%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.) solution of sodium azide (6.2 g, 95 mmol) in water (100 mL) and acetone (100 mL) was added a solution of (E)-3-(2-(2,6-dichlorophenyl)thiazol-4-yl)acryloyl chloride (6.0 g, 19 mmol) in dioxane (100 mL) dropwise. After addition, the resulting mixture was stirred for 1 hour at 0° C. The reaction was quenched with water (50 mL) and extracted with EtOAc (3×80 mL). The combined organic extract was washed with brine (100 mL), dried over Na2SO4 and concentrated under reduced pressure. The resultant residue was purified via silica gel column chromatography eluting with EtOAc/petroleum ether (1:8) to afford the desired product as a yellow solid (6.0 g, 98% yield). LCMS (ESI) m/z: 325.0 [M+H+].

Workup

  1. additionAfter addition
  2. customThe reaction was quenched with water (50 mL)
  3. extractionextracted with EtOAc (3×80 mL)
  4. extractionThe combined organic extract
  5. washwas washed with brine (100 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. customThe resultant residue was purified via silica gel column chromatography
  9. washeluting with EtOAc/petroleum ether (1:8)

Sources & evidence

ORD record
ord-dcc5461345fd492484c4e066e2fdb4fc
Source dataset
uspto-grants-2014_04
Patent number
US08697708B2

Reaction notes

Loading…