Lithium azide → 4-Azidomethyl-2'-cyanobiphenyl

HRID 1198664

反応式

HRID 1198664 の反応式
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]

参加物

4

反応物 2

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

生成物 1

HCID 103539894-Azidomethyl-2'-cyanobiphenyl

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

A mixture of 1.97 g (725 mmole) 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 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.

後処理

  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

出典と根拠

ORDレコード
ord-bff0fe401f214b2c8718e5584330e56e
出典データセット
uspto-grants-1994_01
特許番号
US05281614

関連ノート

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