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

HRID 382354노트

반응식

HRID 382354 반응식
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

참가 물질

5

반응물 3

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 178488846HCID 178488846, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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 (0 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.

후처리

  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 (0 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

출처 및 근거

ORD 기록
ord-659dba3019134a27ae50d5eff4de1377
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06310082B1

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