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Hydrochloric Acid → 2-(4-Chloro-3-methoxy-phenoxymethyl)-1-(3,5-dichloro-benzyl)-1H-imidazole

HRID 2101487
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HRID 2101487 반응식
Cl.Cl[CH2:3][C:4]1[N:5]([CH2:9][C:10]2[CH:15]=[C:14]([Cl:16])[CH:13]=[C:12]([Cl:17])[CH:11]=2)[CH:6]=[CH:7][N:8]=1.[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][C:20]=1[O:26][CH3:27].C([O-])([O-])=O.[K+].[K+].Cl>O.CS(C)=O>[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:3][C:4]2[N:5]([CH2:9][C:10]3[CH:15]=[C:14]([Cl:16])[CH:13]=[C:12]([Cl:17])[CH:11]=3)[CH:6]=[CH:7][N:8]=2)=[CH:21][C:20]=1[O:26][CH3:27]
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참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 110998604-Chloro-3-methoxyphenolHCID 68862721chloromethyl-1-(3,5-dichlorobenzyl)-1H-imidazole hydrochloride

생성물 1

HCID 119517782-(4-Chloro-3-methoxy-phenoxymethyl)-1-(3,5-dichloro-benzyl)-1H-imidazole수율 97.6%

시약·촉매·용매 2

HCID 679
Dimethyl Sulfoxide
용매
HCID 962Water용매

실험 절차

To a mixture of 2-chloromethyl-1-(3,5-dichlorobenzyl)-1H-imidazole hydrochloride (see Example 1) (150 mg, 0.5 mmol), 4-chloro-3-methoxyphenol (158 mg, 1 mmol) and DMSO (1 mL) was added K2CO3 (415 mg, 3 mmol). The reaction was stirred at ambient temperature for 8 h before diluting with water (10 mL). A solution of 1N HCl was added until the mixture was only slightly basic (pH 8) before extracting with EtOAc (30 mL). The EtOAc phase was washed with water (10 mL), dried (Na2SO4) and concentrated in vacuo. The residue was purified by column chromatography (silica gel, 1:2, hexanes/EtOAc) to afford the title compound (194 mg, 97%) as a white solid: ESI MS m/z 397 [C18H15Cl3N2O2+H]+.

후처리

  1. extractionbefore extracting with EtOAc (30 mL)
  2. washThe EtOAc phase was washed with water (10 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography (silica gel, 1:2, hexanes/EtOAc)

출처 및 근거

ORD 기록
ord-90060fad463942c5b7cd8a8acbec1de9
출처 데이터셋
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07572921B2

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