Dichloromethane → 1H-Benzimidazole-7-carboxamide,2-(4-hydroxyphenyl)-

HRID 1870938ノート

反応式

HRID 1870938 の反応式
B(Br)(Br)Br.ClCCl.C[O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[NH:17][C:18]3[C:24]([C:25]([NH2:27])=[O:26])=[CH:23][CH:22]=[CH:21][C:19]=3[N:20]=2)=[CH:12][CH:11]=1>CO>[OH:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]2[NH:20][C:19]3[CH:21]=[CH:22][CH:23]=[C:24]([C:25]([NH2:27])=[O:26])[C:18]=3[N:17]=2)=[CH:14][CH:15]=1

参加物

5

反応物 3

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 178488846HCID 178488846、化合物

生成物 1

HCID 1355464821H-Benzimidazole-7-carboxamide,2-(4-hydroxyphenyl)-

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Under an argon atmosphere 1M boron tribromide in dichloromethane (3.8 ml, 3.79 mmol) was transferred to a flask containing 2-(4'-methoxyphenyl)benzimidazole-4-carboxamide (NU 1076 from Example 5) (202.4 mg, 0.758 mmol). The resulting solution was refluxed for 24 hours using an air condenser. The solvent was removed by distillation to complete dryness. The solid residue was treated with 10% NaOH (10 ml), followed by dropwise addition of concentrated hydrochloric acid to neutralise (pH 7). The white precipitate was collected by filtration and dissolved in ethyl acetate (10 ml). The organic solvent was washed with water (2×3 ml), dried over MgSO4, and the product was obtained by removal of the solvent under reduced pressure. (109.5 mg, 57%). mp 266-267° C.; Found C, 63.27, H 4.37; N 15.67; C14H11N3O2. 0.75 MeOH requires C, 63.04; H, 4.69; N, 15.76; vmax (cm-1) 3424.01, 3384.16, 3309.20, 3249.55, 3155.62, 1642.35, 1618.02, 1594.50, 1577.74; δH 7.03-7.07 (2H, d, J=8.5), 7.34-7.42 (1H, t), 7.75-7.79 (1H, d), 7.85 (1H, br s), 7.90-7.94 (1H, d), 8.15-8.19 (2H, d, J=8.5), 9.4-9.6 (1H, br s), 10.0-10.4 (1H, br s), 13.0-13.4 (1H, br s); m/z (EI) 253 (M+), 236, 208, 93.

後処理

  1. temperatureThe resulting solution was refluxed for 24 hours
  2. customThe solvent was removed by distillation
  3. additionThe solid residue was treated with 10% NaOH (10 ml)
  4. additionfollowed by dropwise addition of concentrated hydrochloric acid
  5. filtrationThe white precipitate was collected by filtration
  6. dissolutiondissolved in ethyl acetate (10 ml)
  7. washThe organic solvent was washed with water (2×3 ml)
  8. dry with materialdried over MgSO4
  9. customthe product was obtained by removal of the solvent under reduced pressure

出典と根拠

ORDレコード
ord-8b09e763015947da935daa20925b5cfd
出典データセット
uspto-grants-2000_08
特許番号
US06100283

反応ノート

読み込み中…