Sodium Carbonate → HCID 136413210, 화합물

HRID 470603노트

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HRID 470603 반응식
C[O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]2[O:17][N:16]=[C:15]([CH2:18][CH2:19][CH3:20])[N:14]=2)[CH:6]=[CH:7][C:8]=1[O:9]C.B(Br)(Br)Br.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl.CO.C(Cl)(Cl)Cl>[CH2:18]([C:15]1[N:14]=[C:13]([CH:12]=[CH:11][C:5]2[CH:4]=[C:3]([OH:2])[C:8]([OH:9])=[CH:7][CH:6]=2)[O:17][N:16]=1)[CH2:19][CH3:20]

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 25134Boron tribromideHCID 673972995-[2-(3,4-Dimethoxy-phenyl)-vinyl]-3-propyl-[1,2,4]oxadiazole

생성물 1

HCID 136413210HCID 136413210, 화합물

시약·촉매·용매 3

HCID 887Methanol용매HCID 6212Chloroform용매HCID 6344Dichloromethane용매2회

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온도
-78 °C

실험 절차

5-[2-(3,4-Dimethoxy-phenyl)-vinyl]-3-propyl-[1,2,4]oxadiazole (compound of Example 3, Method A, Step 1; 1.28 g, 4.66 mmol) was dissolved in dichloromethane (15 mL) and cooled to −78° C. A solution of boron tribromide (4.42 mL, 4.66 mmol) in dichloromethane (5 mL), which was cooled to 0° C., was added slowly over a period of 25 min. After 2 h, the reaction mixture was allowed to warm to room temperature (25° C.) and stirred for 2 h. At the end of the reaction, the mixture was quenched by dropwise addition of methanol (15 mL) at 0° C. and stirred for 20 min at room temperature. The solvent was evaporated and the residue obtained was redissolved in 10% methanol in chloroform at 0° C. and stirred with solid sodium carbonate to obtain pH ˜8. The solvent was evaporated and the crude product obtained was purified by column chromatography (silica gel, 0.5% methanol in chloroform) to afford the title compound.

후처리

  1. additionwas added slowly over a period of 25 min
  2. temperatureto warm to room temperature (25° C.)
  3. customAt the end of the reaction
  4. customthe mixture was quenched by dropwise addition of methanol (15 mL) at 0° C.
  5. stirringstirred for 20 min at room temperature
  6. customThe solvent was evaporated
  7. customthe residue obtained
  8. customto obtain pH ˜8
  9. customThe solvent was evaporated
  10. customthe crude product obtained
  11. customwas purified by column chromatography (silica gel, 0.5% methanol in chloroform)

출처 및 근거

ORD 기록
ord-c8a8179f92994993ac302ebe646bfec9
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08629277B2

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