Chloride → 4-Azido-7-cyanochroman

HRID 32051노트

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HRID 32051 반응식
Cl[CH:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]#[N:13])=[CH:9][CH:10]=2)[O:5][CH2:4][CH2:3]1.[N-:14]=[N+:15]=[N-:16].[Na+].C1(C)C=CC=CC=1.[Cl-]>CN(C=O)C>[N:14]([CH:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]#[N:13])=[CH:9][CH:10]=2)[O:5][CH2:4][CH2:3]1)=[N+:15]=[N-:16]

참가 물질

6

반응물 4

HCID 312ChlorideHCID 1140TolueneHCID 33557Sodium AzideHCID 18448592HCID 18448592, 화합물

생성물 1

HCID 184485894-Azido-7-cyanochroman

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

4-Chloro-7-cyanochroman (Step C) (8.1 g, 42 mmol) was dissolved in dry DMF (90 mL) and NaN3 (4.0 g, 62 mmol) was added and the reaction was heated to 80° C. under N2. After 5 h TLC (SiO2, toluene) showed that no starting chloride was present. The reaction was cooled and partitioned between EtOAc (200 mL) and H2O (150 mL). The organic phase was washed with H2O (2×100 mL) and brine (100 mL). The solution was dried over MgSO4, filtered and concentrated in vacuo to provide a residue which was purified by column chromatography (SiO2, 15% EtOAc in hexane) to provide the title compound.

후처리

  1. temperatureThe reaction was cooled
  2. custompartitioned between EtOAc (200 mL) and H2O (150 mL)
  3. washThe organic phase was washed with H2O (2×100 mL) and brine (100 mL)
  4. dry with materialThe solution was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto provide a residue which
  8. customwas purified by column chromatography (SiO2, 15% EtOAc in hexane)

출처 및 근거

ORD 기록
ord-98fd8387528a469cbcf5e2db00cdee14
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07425631B2

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