Lithium azide → 4-Azidomethyl-2'-cyanobiphenyl

HRID 1198660

反応式

HRID 1198660 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

To a stirred suspension of 20 mmole of 4-bromomethyl-2'-cyanobiphenyl [P. E. Aldrich, M. E. Pierce, and J. J. V. Duncia, European Patent Application 291,969 (1988)] in 55 ml of dry DMSO was added 1.23 g (25 mmole) of freshly pulverized lithium azide, and the mixture was stirred at room temperature under N2. Within a few minutes virtually all of the solid had dissolved, accompanied by a mild exotherm, and this was followed immediately by precipitation of product. After 4 hours the solid was collected on a filter and washed with some methanol, then with a relatively large volume of H2O, and finally again with methanol. The solid was air-dried overnight and then dried further in a vacuum oven at 70° C. (<1 mm) to give white crystals, satisfactory purity by TLC (9:1 hexane-ethyl acetate) for use in the next step. From the combined filtrate and washes was recovered a less pure second crop (cream-colored crystals), which was also usable in the next step. Mass spectrum (FAB) m/e 235 (M+ +1).

後処理

  1. dissolutionWithin a few minutes virtually all of the solid had dissolved
  2. customthis was followed immediately by precipitation of product
  3. customAfter 4 hours the solid was collected on
  4. filtrationa filter
  5. washwashed with some methanol
  6. customThe solid was air-dried overnight
  7. customdried further in a vacuum oven at 70° C. (<1 mm)
  8. customto give white crystals, satisfactory purity by TLC (9:1 hexane-ethyl acetate) for use in the next step
  9. customFrom the combined filtrate and washes was recovered a less pure second crop (cream-colored crystals), which

出典と根拠

ORDレコード
ord-fe8ca6f818114b999c810469276387c3
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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