Lithium azide → 4-Azidomethyl-2'-cyanobiphenyl

HRID 36178

반응식

HRID 36178 반응식
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]#[N:16])=[CH:5][CH:4]=1.[N-:17]=[N+:18]=[N-:19].[Li+]>CS(C)=O>[N:17]([CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]#[N:16])=[CH:5][CH:4]=1)=[N+:18]=[N-:19]

참가 물질

4

반응물 2

HCID 88163Lithium azideHCID 15019124'-(Bromomethyl)-2-cyanobiphenyl

생성물 1

HCID 103539894-Azidomethyl-2'-cyanobiphenyl수율 61%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

A mixture of 1.97 g (725 mole) of 4-bromomethyl-2'-cyanobiphenyl (EP 253,310), 445 mg (9.1 mmole) of lithium azide and 5 ml of dry DMSO was stirred at room temperature under nitrogen for one hour and then partitioned between 100 ml of ether and 100 ml of H2O. The organic phase was washed with 3×100 ml of H2O, then dried (MgSO4), filtered, and concentrated in vacuo to give a residual oil which solidified on standing. This solid was triturated with petroleum ether, collected on a filter, washed with petroleum ether and dried overnight to yield 1.15 g (61%) of the title compound as white crystals, mp 69°-70° C.; mass spectrum (EI) m/e 234 (M+). TLC in 4:1 hexane-EtOAc showed only minor impurities and the material was of sufficient purity to use in the next step.

후처리

  1. custompartitioned between 100 ml of ether and 100 ml of H2O
  2. washThe organic phase was washed with 3×100 ml of H2O
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give a residual oil which
  7. customThis solid was triturated with petroleum ether
  8. customcollected on a filter
  9. washwashed with petroleum ether
  10. customdried overnight

출처 및 근거

ORD 기록
ord-8aaecded671844a2a92627ce27ea0413
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05411980

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