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 1358303노트

반응식

HRID 1358303 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, dt, 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-43e66aa188b24f6e9f1aeb47108eae7d
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06596726B1

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