Sodium Azide → 2-azidomethyl-8-(2-chloro-phenyl)-2H-chromene

HRID 902330ノート

反応式

HRID 902330 の反応式
CC1C=CC(S(O[CH2:12][CH:13]2[CH:22]=[CH:21][C:20]3[C:15](=[C:16]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[Cl:30])[CH:17]=[C:18](F)[CH:19]=3)[O:14]2)(=O)=O)=CC=1.[N-:31]=[N+:32]=[N-:33].[Na+]>CS(C)=O>[N:31]([CH2:12][CH:13]1[CH:22]=[CH:21][C:20]2[C:15](=[C:16]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[Cl:30])[CH:17]=[CH:18][CH:19]=2)[O:14]1)=[N+:32]=[N-:33]

参加物

4

反応物 2

HCID 33557Sodium AzideHCID 86609118[8-(2-chlorophenyl)-6-fluoro-2H-chromen-2-yl]methyl 4-methylbenzenesulfonate

生成物 1

HCID 866091192-azidomethyl-8-(2-chloro-phenyl)-2H-chromene収率 87.8%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

A solution of [8-(2-chlorophenyl)-6-fluoro-2H-chromen-2-yl]methyl 4-methylbenzenesulfonate prepared in Example 61, step 1 (204 mg, 0.459 mmol) and sodium azide (119 mg, 1.834 mmol) in anhydrous dimethyl sulfoxide (8 mL) was heated at 70° C. under nitrogen for 19 hours. The cooled reaction mixture was quenched by the addition of water (30 mL) and the resulting suspension stirred vigorously for 5 minutes. The mixture was then partitioned between ethyl acetate (100 mL) and water (100 mL), the organic phase separated, washed with water (100 mL) and saturated brine (100 mL), dried over magnesium sulfate, filtered and concentrated under reduced pressure to afford 120 mg (67%) of 2-azidomethyl-8-(2-chloro-phenyl)-2H-chromene as a yellow syrup that was used without further purification.

後処理

  1. customThe cooled reaction mixture
  2. customwas quenched by the addition of water (30 mL)
  3. customThe mixture was then partitioned between ethyl acetate (100 mL) and water (100 mL)
  4. customthe organic phase separated
  5. washwashed with water (100 mL) and saturated brine (100 mL)
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-efc3dbebe8d045d88b073649fb9b7a01
出典データセット
uspto-grants-2008_04
特許番号
US07365095B2

反応ノート

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