Thionyl Chloride → 4,6-Dichloro-8-iodo-quinazoline

HRID 1049936ノート

反応式

HRID 1049936 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([I:12])[CH:11]=1)[N:8]=[CH:7][NH:6][C:5]2=O.S(Cl)([Cl:16])=O>CN(C=O)C>[Cl:16][C:5]1[C:4]2[C:9](=[C:10]([I:12])[CH:11]=[C:2]([Cl:1])[CH:3]=2)[N:8]=[CH:7][N:6]=1

参加物

4

反応物 2

HCID 24386Thionyl ChlorideHCID 1363443786-Chloro-8-iodo-4(3H)-quinazolinone

生成物 1

HCID 867039334,6-Dichloro-8-iodo-quinazoline

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To around bottom flask was added 6-chloro-8-iodo-3H-quinazolin-4-one (1000 mg, 3.3 mmol); and thionyl chloride (50 mL). DMF (0.1 mL) was then added, and the reaction was stirred at reflux for 2 h. The reaction was cooled to room temperature, then concentrated via rotovap. The product was then azeotroped 2× with DCM, then dried under vacuum yielding 4,6-dichloro-8-iodo-quinazoline, carried immediately to the next step. 1H NMR (400 MHz, DMSO) δ 9.24-9.20 (s, 1H), 8.77-8.73 (d, J=2.2 Hz, 1H), 8.36-8.31 (d, J=2.2 Hz, 1H).

後処理

  1. temperatureat reflux for 2 h
  2. concentrationconcentrated via rotovap
  3. customThe product was then azeotroped 2× with DCM
  4. customdried under vacuum

出典と根拠

ORDレコード
ord-b5cc936f12de42bd83ce573c6b6ca03d
出典データセット
uspto-grants-2016_07
特許番号
US09382241B2

反応ノート

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