Sodium Azide → 2-(2-Formamidothiazol-4-yl)-2-(2-azidoethoxyimino)acetic acid

HRID 255752ノート

反応式

HRID 255752 の反応式
[N-:1]=[N+:2]=[N-:3].[Na+].[CH:5]([NH:7][C:8]1[S:9][CH:10]=[C:11]([C:13](=[N:17][O:18][CH2:19][CH2:20]Br)[C:14]([OH:16])=[O:15])[N:12]=1)=[O:6].C(=O)(O)[O-].[Na+]>CN(C)C=O.O>[CH:5]([NH:7][C:8]1[S:9][CH:10]=[C:11]([C:13](=[N:17][O:18][CH2:19][CH2:20][N:1]=[N+:2]=[N-:3])[C:14]([OH:16])=[O:15])[N:12]=1)=[O:6]

参加物

6

反応物 3

HCID 33557Sodium AzideHCID 516892Sodium BicarbonateHCID 543016702-(2-Formamidothiazol-4-yl)-2-(2-bromoethoxyimino)acetic acid

生成物 1

HCID 538311562-(2-Formamidothiazol-4-yl)-2-(2-azidoethoxyimino)acetic acid収率 35.7%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 6228Dimethylformamide溶媒

実験手順

Sodium azide (14.87 g.) was added to a solution of 2-(2-formamidothiazol-4-yl)-2-(2- bromoethoxyimino)acetic acid (syn isomer, 15.7 g.) in N,N-dimethylformamide (100 ml.) and water (75 ml.), and stirred at room temperature for 2 days. To the resultant solution was added water (25 ml.) and adjusted to pH 8.0 with a saturated aqueous solution of sodium bicarbonate. The solution was washed with ethyl acetate (250 ml.). The solution was adjusted to pH 2.5 and extracted with ethyl acetate (350 ml.). The extract was washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and concentrated in vacuo. The residue was recrystalized from a solution of acetone and methylene chloride (3:1) repeatedly. The precipitates were collected by filtration to give 2-(2-formamidothiazol-4-yl)-2-(2-azidoethoxyimino)acetic acid (syn isomer, 4.95 g.).

後処理

  1. washThe solution was washed with ethyl acetate (250 ml.)
  2. extractionextracted with ethyl acetate (350 ml.)
  3. washThe extract was washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was recrystalized from a solution of acetone and methylene chloride (3:1) repeatedly
  7. filtrationThe precipitates were collected by filtration

出典と根拠

ORDレコード
ord-211cd157bbb44026b035cc2536d551dc
出典データセット
uspto-grants-1987_10
特許番号
US04698337

反応ノート

読み込み中…