Thionyl Chloride → HCID 60069839, compound

HRID 549281Notes

Reaction equation

HRID 549281 reaction equation
S(Cl)(Cl)=O.[Br:5][C:6]1[S:10][C:9](/[CH:11]=[CH:12]/[C:13]([OH:15])=O)=[CH:8][CH:7]=1.[N-:16]=[N+:17]=[N-:18].[Na+].O1CCOCC1>C(Cl)(Cl)Cl.O>[Br:5][C:6]1[S:10][C:9](/[CH:11]=[CH:12]/[C:13]([N:16]=[N+:17]=[N-:18])=[O:15])=[CH:8][CH:7]=1

Participants

7

Reactant 4

HCID 24386Thionyl ChlorideHCID 312751,4-DioxaneHCID 33557Sodium AzideHCID 2059999(2E)-3-(5-BROMO(2-THIENYL))PROP-2-ENOIC ACID

Product 1

HCID 60069839HCID 60069839, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Conditions

Temperature
75 °C

Procedure

Thionyl chloride (1.04 mL) was added to a solution of (2E)-3-(5-bromothien-2-yl) acrylic acid (1.04 g, 4.46 mmol) in chloroform (20 mL) and the mixture was refluxed for 2 h at 75° C. and than used in the next step. The above solution was added drop wise to a stirred suspension of sodium azide (0.58 g, 8.93 mmol), dioxane (3 mL) and water (3 mL) in an ice bath. After 10 min a precipitate appeared which was filtered off and washed with water. The residue was dissolved in dichloromethane, dried with MgSO4, filtered and the solvent was removed to afford: 0.96 g (83.4%). 1H NMR (270 MHz CH3OH-d4) δ ppm 6.20 (d, J=15.57 Hz, 1H) 7.15-7.25 (m, 2H) 7.80 (d, J=15.57 Hz, 1H); MS 258.1 (M−H)+; Purity (HPLC) 65%.

Workup

  1. additionThe above solution was added drop
  2. filtrationwhich was filtered off
  3. washwashed with water
  4. dissolutionThe residue was dissolved in dichloromethane
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. customthe solvent was removed
  8. customto afford

Sources & evidence

ORD record
ord-b62f353612ec455d8e0ee17d188826fc
Source dataset
uspto-grants-2011_05
Patent number
US07943639B2

Reaction notes

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