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Pyridine → [(4E)-4-benzoyloxyimino-2-[[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]methyl]-2,5,7,8-tetramethyl-3H-chromen-6-yl] benzoate

HRID 1030364
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HRID 1030364 반응식
[OH:1][C:2]1[C:3]([CH3:33])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7]([CH2:15][O:16][C:17]1[CH:30]=[CH:29][C:20]([CH2:21][CH:22]3[S:26][C:25](=[O:27])[NH:24][C:23]3=[O:28])=[CH:19][CH:18]=1)([CH3:14])[CH2:6]/[C:5]/2=[N:31]\[OH:32].[C:34](Br)(=[O:41])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.N1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1.C(=O)([O-])[O-].[K+].[K+].C([O:58][CH2:59][CH3:60])(=O)C>CN(C)C=O>[C:34]([O:1][C:2]1[C:3]([CH3:33])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7]([CH2:15][O:16][C:17]1[CH:18]=[CH:19][C:20]([CH2:21][CH:22]3[S:26][C:25](=[O:27])[NH:24][C:23]3=[O:28])=[CH:29][CH:30]=1)([CH3:14])[CH2:6]/[C:5]/2=[N:31]\[O:32][C:59](=[O:58])[C:60]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)(=[O:41])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 5

HCID 1049PyridineHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 12056Benzoyl bromideHCID 883935005-[[4-[[(4E)-6-hydroxy-4-hydroxyimino-2,5,7,8-tetramethyl-3H-chromen-2-yl]methoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione

생성물 1

HCID 19822268
[(4E)-4-benzoyloxyimino-2-[[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]methyl]-2,5,7,8-tetramethyl-3H-chromen-6-yl] benzoate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of 1 g of 5-{4-[6-hydroxy-4-(E)-hydroxyimino-2,5,7,8tetramethylchroman-2-ylmethoxy ]benzyl}-thiazolidine-2,4-dione (prepared as described in Example 13), 1.7 g of benzoyl bromide, 10 ml of pyridine and 5 ml of dimethylformamide was allowed to stand for 6 days at room temperature, after which it was heated for 8 hours at 60°-80° C. An aqueous solution of potassium carbonate and ethyl acetate were then added to the reaction mixture. The organic layer was separated and dried over anhydrous sodium sulfate. The solvent was distilled off and the residue was purified by silica gel column chromatography eluted with a 4:3 by volume mixture of hexane and ethyl acetate, to give the title compound, softening at 101°-107° C.

후처리

  1. temperatureafter which it was heated for 8 hours at 60°-80° C
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off
  5. customthe residue was purified by silica gel column chromatography
  6. washeluted with a 4:3 by volume mixture of hexane and ethyl acetate

출처 및 근거

ORD 기록
ord-0b1aa97384c849a7acbc759e32f90111
출처 데이터셋
uspto-grants-1992_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05104888

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