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Hydrochloric Acid → N-(aminocarbonyl)-1-(4-chlorobenzoyl)-N-hydroxy-5-methoxy-2-methyl-1H-indole-3-methanamine

HRID 1461445
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인쇄 미리보기

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HRID 1461445 반응식
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([C:6]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=3)[C:10]([CH2:19][NH:20][OH:21])=[C:9]2[CH3:22])=[O:7])=[CH:4][CH:3]=1.[N-:25]=[C:26]=[O:27].[Na+].Cl>O1CCOCC1.O.C(OCC)(=O)C>[NH2:25][C:26]([N:20]([OH:21])[CH2:19][C:10]1[C:11]2[C:16](=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=2)[N:8]([C:6](=[O:7])[C:5]2[CH:23]=[CH:24][C:2]([Cl:1])=[CH:3][CH:4]=2)[C:9]=1[CH3:22])=[O:27]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 313Hydrochloric AcidHCID 11051568NaNCOHCID 150273901-(4-Chlorobenzoyl)-N-hydroxy-5-methoxy-2-methyl-1H-indole-3-methanamine

생성물 1

HCID 15027396N-(aminocarbonyl)-1-(4-chlorobenzoyl)-N-hydroxy-5-methoxy-2-methyl-1H-indole-3-methanamine수율 53.3%

시약·촉매·용매 3

HCID 962Water용매
HCID 8857
Ethyl Acetate
용매
HCID 312751,4-Dioxane용매

실험 절차

To a suspension of 1-(4-chlorobenzoyl)-N-hydroxy-5-methoxy-2-methyl-lH-indole-3-methanamine (500 mg, 1.45 mmol) in 30 ml of 1,4-dioxane and 15 ml of water at 0° C. is added sodium isocyanate (104 mg, 1.59 mmol) followed by 1.59 ml (1.59 mmol) of 1N hydrochloric acid. The reaction mixture is diluted with ethyl acetate and washed once with water, and finally with a saturated solution of sodium chloride. It is further dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude residue is recrystallized from methylene chloride and dried to give 300 mg (53%) of pure N-(aminocarbonyl)-1-(4-chlorobenzoyl)-N-hydroxy-5-methoxy-2-methyl-lH-indole -3-methanamine (535); mp 151.5°-154° C. dec.

후처리

  1. washwashed once with water
  2. dry with materialIt is further dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude residue is recrystallized from methylene chloride
  6. customdried

출처 및 근거

ORD 기록
ord-d266b5b1acd94d54b40a1ece8cf64daf
출처 데이터셋
uspto-grants-1991_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05075330

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