Propargyl bromide → Ethyl 2-(2-tritylaminothiazol-4-yl)-2-propargyloxyiminoacetate

HRID 435274노트

반응식

HRID 435274 반응식
[CH2:1](Br)[C:2]#[CH:3].[C:5]([NH:24][C:25]1[S:26][CH:27]=[C:28]([C:30](=[N:36][OH:37])[C:31]([O:33][CH2:34][CH3:35])=[O:32])[N:29]=1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:5]([NH:24][C:25]1[S:26][CH:27]=[C:28]([C:30](=[N:36][O:37][CH2:3][C:2]#[CH:1])[C:31]([O:33][CH2:34][CH3:35])=[O:32])[N:29]=1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

참가 물질

5

반응물 3

HCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 6802348Ethyl 2-(2-tritylamino-4-thiazolyl)-2-hydroxyiminoacetate

생성물 1

HCID 54124335Ethyl 2-(2-tritylaminothiazol-4-yl)-2-propargyloxyiminoacetate수율 77%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Propargyl bromide (4.16 g.) was added to a suspension of ethyl 2-(2-tritylaminothiazol-4-yl)-2-hydroxyiminoacetate (syn isomer, 10 g.), potassium carbonate (4.84 g.) and N,N-dimethylformamide (22 ml.) under atmosphere of nitrogen gas and stirred at room temperature for 100 minutes. The insoluble substance was filtered off and washed with a little of N,N-dimethylformamide. The filtrate and washing solution were combined together, and water (400 ml.) was added to the solution. After the suspension was extracted with ethyl acetate (400 ml.), the extract was washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. After treating the solution with activated charcoal, the solution was concentrated in vacuo. The residue was triturated with diisopropyl ether. The precipitates were collected by filtration, and washed with diisopropyl ether to give ethyl 2-(2-tritylaminothiazol-4-yl)-2-propargyloxyiminoacetate (syn isomer, 8.34 g.).

후처리

  1. filtrationThe insoluble substance was filtered off
  2. washwashed with a little of N,N-dimethylformamide
  3. washThe filtrate and washing solution
  4. additionwater (400 ml.) was added to the solution
  5. extractionAfter the suspension was extracted with ethyl acetate (400 ml.)
  6. washthe extract was washed with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over magnesium sulfate
  8. additionAfter treating the solution with activated charcoal
  9. concentrationthe solution was concentrated in vacuo
  10. customThe residue was triturated with diisopropyl ether
  11. filtrationThe precipitates were collected by filtration
  12. washwashed with diisopropyl ether

출처 및 근거

ORD 기록
ord-5537b0307c7344c382a333f53719a103
출처 데이터셋
uspto-grants-1983_08
특허 번호
US04400379

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