Acetic Acid → 2-Iodo-1-triphenylmethylimidazole-4-carboxylic acid

HRID 1108277노트

반응식

HRID 1108277 반응식
[I:1][C:2]1[N:3]([C:11]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:4]=[C:5]([C:7]([O:9]C)=[O:8])[N:6]=1.C(O)(=O)C>[OH-].[Na+].C(OCC)(=O)C>[I:1][C:2]1[N:3]([C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:4]=[C:5]([C:7]([OH:9])=[O:8])[N:6]=1

참가 물질

5

반응물 2

HCID 176Acetic AcidHCID 187846292-Iodo-4-(methoxycarbonyl)-1-triphenylmethylimidazole

생성물 1

HCID 187846222-Iodo-1-triphenylmethylimidazole-4-carboxylic acid수율 87%

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 14798Sodium Hydroxide용매

실험 절차

A suspension of 2-iodo-4-(methoxycarbonyl)-1-triphenylmethylimidazole (1.978 g, 4 mmol) in 6N sodium hydroxide (15 mL) was heated at reflux for 4 hours. The resulting suspension was diluted with ethyl acetate (20 mL) and then slightly acidified with acetic acid. The resulting clear solution was extracted three times with ethyl acetate (20 mL) and the combined extracts were dried (magnesium sulfate) and concentrated in vacuo. Residual acetic acid was removed under high vacuum to give 2-iodo-1-triphenylmethylimidazole-4-carboxylic acid (1.67 g, 87%) as a white solid, mp 203-205° C.: 1H NMR (CDCl3) δ 7.60 (s, 1H), 7.38-7.20 (m, 9H), 7.18-7.09 (m, 6H).

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 4 hours
  3. extractionThe resulting clear solution was extracted three times with ethyl acetate (20 mL)
  4. dry with materialthe combined extracts were dried (magnesium sulfate)
  5. concentrationconcentrated in vacuo
  6. customResidual acetic acid was removed under high vacuum

출처 및 근거

ORD 기록
ord-38dccbc51e5f4004ba82d8989d029d56
출처 데이터셋
uspto-grants-2000_05
특허 번호
US06066639

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