Thionyl Chloride → HCID 60069839、化合物

HRID 549281ノート

反応式

HRID 549281 の反応式
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

参加物

7

反応物 4

HCID 24386Thionyl ChlorideHCID 312751,4-DioxaneHCID 33557Sodium AzideHCID 2059999(E)-3-(5-Bromothiophen-2-YL)acrylic acid

生成物 1

HCID 60069839HCID 60069839、化合物

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6212Chloroform溶媒

反応条件

温度
75 °C

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-b62f353612ec455d8e0ee17d188826fc
出典データセット
uspto-grants-2011_05
特許番号
US07943639B2

反応ノート

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