Water → 6-Chloro-8-oxa-3,5-diazatricyclo[7.4.0.0,2,7]trideca-1(9),2(7),3,5,10,12-hexaene

HRID 1489621노트

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HRID 1489621 반응식
CN(C=O)C.[C:6](Cl)([C:8]([Cl:10])=O)=[O:7].[N:12]1[C:17]2[C:18]3[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=3OC=2C(=O)[NH:14][CH:13]=1.O>ClCCCl>[Cl:10][C:8]1[C:6]2[O:7][C:19]3[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=3[C:17]=2[N:12]=[CH:13][N:14]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 1354154698-Oxa-3,5-diazatricyclo[7.4.0.0,2,7]trideca-1(13),2(7),3,9,11-pentaen-6-one

생성물 1

HCID 6092956-Chloro-8-oxa-3,5-diazatricyclo[7.4.0.0,2,7]trideca-1(9),2(7),3,5,10,12-hexaene수율 93%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

반응 조건

온도
25 °C

실험 절차

DMF (0.23 mL, 3.1 mmol) is added dropwise to a solution of (COCl)2 (0.28 mL, 3.1 mmol) in 1,2-dichloroethane (15 mL) at 25° C. After gas evolution ceases, 3H-benzofurano[3,2-d]pyrimid-4-one (113 mg, 0.61 mmol) is added. The resulting mixture is heated at reflux for 1 h. After the reaction has cooled to 25° C., water is added and the resulting mixture is extracted with CHCl3. The combined extracts are washed with water, saturated brine and dried (MgSO4). The solvent is removed under reduced pressure to give 4-chlorobenzofurano[3,2-d]pyrimidine (116 mg, 93%) as a yellow solid. 1H NMR (DMSO) δ9.08 (1H, s), 8.30 (1H, d. J=8.1 Hz), 8.02 (1H, d, J=8.5 Hz), 7.90, (1H, dr, Jd =1.3 Hz, Jt =7.1 Hz), 7.64 (1H, dt, Jd =1.0 Hz, Jt =7.8 Hz).

후처리

  1. temperatureThe resulting mixture is heated
  2. temperatureat reflux for 1 h
  3. extractionthe resulting mixture is extracted with CHCl3
  4. washThe combined extracts are washed with water, saturated brine
  5. dry with materialdried (MgSO4)
  6. customThe solvent is removed under reduced pressure

출처 및 근거

ORD 기록
ord-76027ffda55346199e3154353ce39d6e
출처 데이터셋
uspto-grants-1997_10
특허 번호
US05679683

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