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Hydrochloric Acid → 2-(2,4-dichlorophenyl)-5-methyl-1-(4-methoxyphenyl)-1H-imidazole-4-carboxylic acid

HRID 2215061
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HRID 2215061 반응식
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[C:11]([CH3:19])=[C:12]([C:14]([O:16]CC)=[O:15])[N:13]=1.[Li+].[OH-].O.Cl>C1COCC1.C(OC(=O)C)C>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]([C:20]2[CH:21]=[CH:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=2)[C:11]([CH3:19])=[C:12]([C:14]([OH:16])=[O:15])[N:13]=1
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참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 962Water2회HCID 3939Lithium HydroxideHCID 11188916ethyl 2-(2,4-dichlorophenyl)-1-(4-methoxyphenyl)-5-methyl-1H-imidazole-4-carboxylate

생성물 1

HCID 111997572-(2,4-dichlorophenyl)-5-methyl-1-(4-methoxyphenyl)-1H-imidazole-4-carboxylic acid수율 87%

시약·촉매·용매 2

HCID 8028
Tetrahydrofuran
용매
HCID 8857Ethyl Acetate용매

반응 조건

온도
80 °C

실험 절차

Part B: To a stirred solution of ethyl 2-(2,4-dichlorophenyl)-5-methyl-1-(4-methoxyphenyl)-1H-imidazole-4-carboxylate (8.00 gram, 0.0198 mol) in THF (80 mL) is added LiOH (0.59 gram, 2 molar equivalents) and water (80 mL). The resulting mixture is stirred for 16 hours at 80° C. After cooling to room temperature, HCl (2N solution, 12.3 mL) is added to give an oily precipitate. After addition of water and extraction with ethylacetate, the ethylacetate layer is collected, dried over Na2SO4, filtered and concentrated in vacuo. The residue is crystallised from diisopropyl ether and dried to give 2-(2,4-dichlorophenyl)-5-methyl-1-(4-methoxyphenyl)-1H-imidazole-4-carboxylic acid (4.04 gram, 87% yield) as a pale grey solid. Melting point: 189–191° C.

후처리

  1. temperatureAfter cooling to room temperature
  2. customto give an oily precipitate
  3. customthe ethylacetate layer is collected
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue is crystallised from diisopropyl ether
  8. customdried

출처 및 근거

ORD 기록
ord-98535637c1734d6dbe340367f71b75d8
출처 데이터셋
uspto-grants-2006_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07109216B2

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