Thioacetamide → 7-bromo-4-(2-methyl-1,3-thiazol-4-yl)-2H-chromen-2-one

HRID 1988213

반응식

HRID 1988213 반응식
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:13](=O)[CH2:14]Br)=[CH:7][C:8](=[O:12])[O:9]2)=[CH:4][CH:3]=1.[C:17]([NH2:20])(=[S:19])[CH3:18]>CN(C=O)C>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:13]3[N:20]=[C:17]([CH3:18])[S:19][CH:14]=3)=[CH:7][C:8](=[O:12])[O:9]2)=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 2723949ThioacetamideHCID 233702397-bromo-4-(bromoacetyl)-2H-chromen-2-one

생성물 1

HCID 598148377-bromo-4-(2-methyl-1,3-thiazol-4-yl)-2H-chromen-2-one

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

To a solution of 7-bromo-4-(bromoacetyl)-2H-chromen-2-one (0.605 g, 1.7 mmol) in DMF is added thioacetamide (0.138 g, 1.8 mmol). The mixture is stirred 24 h at rt and at 100° C. overnight. Once cool to rt, it is partitioned between aqueous NH4Cl and EtOAc. The layers are separated and the aqueous phase is extracted with EtOAc. The combined organic layers are washed with brine and dried over anhydrous Na2SO4. The solvent is evaporated and the residue swished in hexanes/Et2O to give the title compound.

후처리

  1. temperatureOnce cool to rt
  2. customit is partitioned between aqueous NH4Cl and EtOAc
  3. customThe layers are separated
  4. extractionthe aqueous phase is extracted with EtOAc
  5. washThe combined organic layers are washed with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. customThe solvent is evaporated

출처 및 근거

ORD 기록
ord-ab26fd90653f4774805dbe4a8147a319
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07553973B2

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