Triethylamine → 2-{4-[(2-Phenylimidazol-5-yl)methyl]piperazinyl}quinazoline

HRID 1276597ノート

反応式

HRID 1276597 の反応式
[C:1]1([C:7]2[NH:8][CH:9]=[C:10]([CH2:12]O)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[N:16][C:15]=1[N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1.C(N(CC)CC)C>S(Cl)(Cl)=O>[C:1]1([C:7]2[NH:11][C:10]([CH2:12][N:27]3[CH2:28][CH2:29][N:24]([C:15]4[N:16]=[CH:17][C:18]5[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=5)[N:14]=4)[CH2:25][CH2:26]3)=[CH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 64232662-Piperazin-1-yl-quinazolineHCID 10080865(2-Phenyl-1H-imidazol-5-yl)methanol

生成物 1

HCID 99293032-{4-[(2-Phenylimidazol-5-yl)methyl]piperazinyl}quinazoline収率 86.4%

試薬・触媒・溶媒 1

HCID 24386Thionyl Chloride溶媒

実験手順

A sample of 2-phenyl-4-hydroxymethylimidazole (348 mg, 2 mmol) is heated for 5 min in thionyl chloride (5 mL) and subsequently concentrated. Chloroform (10 mL) is added and the solution reconcentrated. The resulting dark oil is then taken up in chloroform (10 mL) and treated with 1-quinazolin-2-ylpiperazine (428 mg, 2 mmol) and triethyl amine (2 mL). After 10 minutes, the reaction is washed with 2N NaOH solution, dried (Na2SO4) and concentrated to provide the title compound (Compound 4) as an oil (640 mg), the hydrochloride salt is prepared in a conventional manner, m.p. 101-105° C. (Compound 4a). 1H NMR (CDCl3) 9.0 (s, 1H), 7.9 (d, J=7 Hz, 2H), 7.65 (m, 2H), 7.55 (d, J=6 Hz, 1H), 7.2-7.4 (m, 4H), 7.0 (s, 1H, imidazole CH), 3.95 (m, 4H), 3.6 (s, 2H), 2.6 (t, J=5 Hz, 4H).

後処理

  1. concentrationsubsequently concentrated
  2. additionChloroform (10 mL) is added
  3. washthe reaction is washed with 2N NaOH solution
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-eddf2b4297e94ff8952007cd734576bb
出典データセット
uspto-grants-2000_12
特許番号
US06166205

反応ノート

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