Formamide → 4-Chloroquinazoline

HRID 487577

반응식

HRID 487577 반응식
[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

참가 물질

8

반응물 5

HCID 713FormamideHCID 9210QuinazolineHCID 24819Phosphorus pentachlorideHCID 11008255Gold's ReagentHCID 178517962HCID 178517962, 화합물

생성물 1

HCID 788644-Chloroquinazoline

시약·촉매·용매 2

HCID 24813Phosphorus oxychloride용매HCID 312751,4-Dioxane용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-6a3211e780de4b41a12fb9630be8eae3
출처 데이터셋
uspto-grants-1994_03
특허 번호
US05296484

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