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

HRID 255752노트

반응식

HRID 255752 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매2회HCID 6228Dimethylformamide용매

실험 절차

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.).

후처리

  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

출처 및 근거

ORD 기록
ord-211cd157bbb44026b035cc2536d551dc
출처 데이터셋
uspto-grants-1987_10
특허 번호
US04698337

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