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 1489621ノート

反応式

HRID 1489621 の反応式
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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

反応条件

温度
25 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-76027ffda55346199e3154353ce39d6e
出典データセット
uspto-grants-1997_10
特許番号
US05679683

反応ノート

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