Lithium azide → 5-[4'-(Azidomethyl)[1,1'-biphenyl]-2-yl]-1-(triphenylmethyl)-1H-tetrazole

HRID 36172

反応式

HRID 36172 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]2[N:19]([C:20]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[N:18]=[N:17][N:16]=2)=[CH:5][CH:4]=1.[N-:39]=[N+:40]=[N-:41].[Li+]>CS(C)=O>[N:39]([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]2[N:19]([C:20]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[N:18]=[N:17][N:16]=2)=[CH:5][CH:4]=1)=[N+:40]=[N-:41]

参加物

4

反応物 2

HCID 88163Lithium azideHCID 100534615-(4'-(Bromomethyl)(1,1'-biphenyl)-2-yl)-1-trityl-1H-tetraazole

生成物 1

HCID 149873355-[4'-(Azidomethyl)[1,1'-biphenyl]-2-yl]-1-(triphenylmethyl)-1H-tetrazole収率 83%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

To a stirred suspension of 11.15 g (20 mmole) of 5-[4'-(bromomethyl)biphenyl-2-yl]-N-trityltetrazole [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 8.60 g (83%) of white crystals, mp 139°-140.5° C. dec., 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 (1.68 g of cream-colored crystals, mp 129°-132° C. dec.), which was also usable in the next step. Mass spectrum (FAB) m/e 243 (trityl cation); IR (Nujol) 2100 cm-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)

出典と根拠

ORDレコード
ord-d88b97170b63494792f91d22e2328ab6
出典データセット
uspto-grants-1995_05
特許番号
US05411980

関連ノート

読み込み中…