Sodium Azide → HCID 86723302, compound

HRID 2366192Notes

Reaction equation

HRID 2366192 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[Cl:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([F: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]([F: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 86723301HCID 86723301, compound

Product 1

HCID 86723302HCID 86723302, compoundYield 90.4%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.) solution of NaN3 (6.2 g, 95 mmol) in water (100 mL) and acetone (100 mL) was added a solution of (E)-3-(2-(2-chloro-6-fluorophenyl)thiazol-4-yl)acryloyl chloride (5.7 g, 19 mmol) in dioxane (100 mL) dropwise over 15 minutes. After addition, the resulting mixture was stirred for another 1 hour at 0° C. The reaction was quenched with water (50 mL) and extracted with EtOAc (3×100 mL). The combined organic extract was washed brine (100 mL), dried over Na2SO4, and concentrated under reduced pressure. The residue was purified with silica gel column chromatography, eluting with EtOAc/petroleum ether (1:8) to give the desired product as a yellow solid (5.3 g, 90% yield). LCMS (ESI) m/z: 309.0 [M+H+].

Workup

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

Sources & evidence

ORD record
ord-d49b09d19b8d4f41b2dd57ce3412912c
Source dataset
uspto-grants-2014_04
Patent number
US08697708B2

Reaction notes

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