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

HRID 902330노트

반응식

HRID 902330 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-efc3dbebe8d045d88b073649fb9b7a01
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07365095B2

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