Sodium Azide → 2-Azidomethyl-8-(2-chloro-phenyl)-6-fluoro-chroman

HRID 902313노트

반응식

HRID 902313 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:9]=[C:10]([F:30])[CH:11]=[C:12]2[C:17]=1[O:16][CH:15]([CH2:18]OS(C1C=CC(C)=CC=1)(=O)=O)[CH2:14][CH2:13]2.[N-:31]=[N+:32]=[N-:33].[Na+]>CS(C)=O>[N:31]([CH2:18][CH:15]1[CH2:14][CH2:13][C:12]2[C:17](=[C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])[CH:9]=[C:10]([F:30])[CH:11]=2)[O:16]1)=[N+:32]=[N-:33]

참가 물질

4

반응물 2

HCID 33557Sodium AzideHCID 86609109Toluene-4-sulfonic acid 8-(2-chloro-phenyl)-6-fluoro-chroman-2-ylmethyl ester

생성물 1

HCID 866091102-Azidomethyl-8-(2-chloro-phenyl)-6-fluoro-chroman수율 95%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

A solution of toluene-4-sulfonic acid 8-(2-chloro-phenyl)-6-fluoro-chroman-2-ylmethyl ester (253 mg, 0.566 mmol) and sodium azide (147 mg, 2.264 mmol) in anhydrous dimethyl sulfoxide (8 mL) was heated to 70° C. under nitrogen for 20 hours. The cooled reaction mixture was quenched by the addition of water (30 mL) and the resulting suspension stirred vigorously for 10 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 170 mg (95%) of 2-azidomethyl-8-(2-chloro-phenyl)-6-fluoro-chroman a colorless syrup.

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-57c76d60b92c48a7af4887ad66e9af76
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07365095B2

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