Stannous Chloride → HCID 67199100、化合物

HRID 545511ノート

反応式

HRID 545511 の反応式
[N:1]([O-])=O.[Na+].[F:5][C:6]1([F:16])[O:10][C:9]2[CH:11]=[CH:12][C:13]([NH2:15])=[CH:14][C:8]=2[O:7]1.[Sn](Cl)[Cl:18]>O.Cl>[ClH:18].[F:16][C:6]1([F:5])[O:10][C:9]2[CH:11]=[CH:12][C:13]([NH:15][NH2:1])=[CH:14][C:8]=2[O:7]1

参加物

6

反応物 3

HCID 24479Stannous ChlorideHCID 27368935-Amino-2,2-difluoro-1,3-benzodioxoleHCID 23668193Sodium Nitrite

生成物 1

HCID 67199100HCID 67199100、化合物収率 26%

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒2 回HCID 962Water溶媒2 回

実験手順

Add slowly a solution of sodium nitrite (1.40 g, 20.3 mmol) in water (11 mL) to a flask containing 2,2-difluoro-benzo[1,3]dioxol-5-ylamine (3.41 g, 19.7 mmol), water (14 mL), and concentrated hydrochloric acid (5 mL) at −5° C. Cool the reaction to −10° C. then add tin(II) chloride (11.20 g, 49.6 mmol) in concentrated hydrochloric acid (9 mL). Stir the reaction for one hour and collect the resultant solid by filtration. Dissolve the solid in methylene chloride (20 mL) and treat with acetone (5 mL). Wash the resultant organic solution with water (50 mL), dry over magnesium sulfate, filter, and evaporate under reduced pressure. Stir the resultant oil with 2N hydrochloric acid (100 mL) for 12 h. Collect a solid by filtration, wash with water and dry in a vacuum oven at 40° C. overnight to give the subtitled compound (1.14 g, 26%) as a red powder. 1H NMR (300 MHz, DMSO-d6): δ 10.32 (br s, 3H), 8.45 (br s, 1H), 7.34 (d, J=8.7 Hz, 1H), 7.11 (d, J=2.3 Hz, 1H), 6.79 (dd, J=8.7, 2.3 Hz, 1H).

後処理

  1. temperatureCool
  2. customthe reaction to −10° C.
  3. customthe reaction for one hour
  4. customcollect the resultant solid
  5. filtrationby filtration
  6. dissolutionDissolve the solid in methylene chloride (20 mL)
  7. additiontreat with acetone (5 mL)
  8. washWash the resultant organic solution with water (50 mL)
  9. dry with materialdry over magnesium sulfate
  10. filtrationfilter
  11. customevaporate under reduced pressure
  12. stirringStir the resultant oil with 2N hydrochloric acid (100 mL) for 12 h
  13. customCollect a solid
  14. filtrationby filtration
  15. washwash with water
  16. customdry in a vacuum oven at 40° C. overnight

出典と根拠

ORDレコード
ord-b4b1fbd7325c4a49bc00a6aff55040b8
出典データセット
uspto-grants-2011_05
特許番号
US07935722B2

反応ノート

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