Formamide → 4-Chloroquinazoline

HRID 487577ノート

反応式

HRID 487577 の反応式
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[N:3][CH:2]=1.C(N)=O.CN(C=NC=[N+](C)C)C.[Cl-].OC1C2C(=CC=CC=2)N=CN=1.P(Cl)(Cl)(Cl)(Cl)[Cl:36]>O1CCOCC1.P(Cl)(Cl)(Cl)=O>[Cl:36][C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:1]=[CH:2][N:3]=1

参加物

8

反応物 5

HCID 713FormamideHCID 9210QuinazolineHCID 24819Phosphorus pentachlorideHCID 11008255Gold's ReagentHCID 178517962HCID 178517962、化合物

生成物 1

HCID 788644-Chloroquinazoline

試薬・触媒・溶媒 2

HCID 24813Phosphorus oxychloride溶媒HCID 312751,4-Dioxane溶媒

実験手順

Quinazoline starting materials are commercially available or readily prepared using conventional procedures. For example, 4-hydroxy quinazolines can be prepared from commercially available anthranilic acids via condensation with excess formamide at reflux (M. Endicott et al. J. Am. Chem. Soc., 1946, 68, 1299). Alternatively hydroxy quinazolines can be prepared in dioxane at reflux using Gold's reagent (J. Gupton; Correia, K.; Hertel, G. Synthetic Communications, 1984, 14, 1013). Once in hand, the 4-hydroxy quinazoline is chlorinated under standard conditions, using for example phosphorus pentachloride in phosphorus oxychloride, to provide 4-chloroquinazoline starting materials. The 4-hydroxy quinazoline derivatives can advantageously be chlorinated using the chlorinating reagents and procedure disclosed in U.S. Pat. No. 4,230,644.

後処理

  1. customreadily prepared
  2. temperatureat reflux (M. Endicott et al. J. Am. Chem. Soc., 1946, 68, 1299)
  3. temperatureat reflux

出典と根拠

ORDレコード
ord-6a3211e780de4b41a12fb9630be8eae3
出典データセット
uspto-grants-1994_03
特許番号
US05296484

反応ノート

読み込み中…