Acetic Acid → 5-{4-[2-(5-Methyl-2-phenyl-4-oxazolyl)-2-oxoethoxy]benzylidene}-2,4-thiazolidinedione

HRID 4394

반응식

HRID 4394 반응식
[H-].[Na+].[OH:3][C:4]1[CH:17]=[CH:16][C:7]([CH:8]=[C:9]2[S:13][C:12](=[O:14])[NH:11][C:10]2=[O:15])=[CH:6][CH:5]=1.Br[CH2:19][C:20]([C:22]1[N:23]=[C:24]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[O:25][C:26]=1[CH3:27])=[O:21].C(O)(=O)C>CN(C)C=O>[CH3:27][C:26]1[O:25][C:24]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[N:23][C:22]=1[C:20](=[O:21])[CH2:19][O:3][C:4]1[CH:17]=[CH:16][C:7]([CH:8]=[C:9]2[S:13][C:12](=[O:14])[NH:11][C:10]2=[O:15])=[CH:6][CH:5]=1

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 5178225-((4-Hydroxyphenyl)methylene)-2,4-thiazolidinedioneHCID 149136502-Bromo-1-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethan-1-one

생성물 1

HCID 539081335-{4-[2-(5-Methyl-2-phenyl-4-oxazolyl)-2-oxoethoxy]benzylidene}-2,4-thiazolidinedione수율 33.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

60% sodium hydride in oil (0.24 g) was added to a solution of 5-(4-hydroxybenzylidene)-2,4-thiazolidinedione (0.663 g) in N,N-dimethylformamide (20 ml) and the mixture was stirred for 30 minutes. Then, a solution of 4-bromoacetyl-5-methyl-2-phenyloxazole (0.841 g) in N,N-dimethylformamide (10 ml) was added dropwise to the mixture under ice-cooling. After stirring under ice-cooling for 30 minutes, the reaction solution was poured into ice-cold water. The aqueous mixture was made acid with acetic acid. The solid which precipitated was collected by filtration, washed with water, and crystallized from acetone to give 5-{4-[2-(5-methyl-2-phenyl-4-oxazolyl)-2-oxoethoxy]benzylidene}-2,4-thiazolidinedione (0.42 g, 32.3%). Recrystallization from chloroform-ethanol yielded colorless needles, m.p. 244°-245° C. Elemental analysis for C22H16N2O5S, Calcd.: C, 62.85; H, 3.84; N, 6.66. Found: C, 62.80; H, 3.69; N, 6.93.

후처리

  1. temperaturecooling
  2. stirringAfter stirring under ice-
  3. temperaturecooling for 30 minutes
  4. additionthe reaction solution was poured into ice-cold water
  5. customThe solid which precipitated
  6. filtrationwas collected by filtration
  7. washwashed with water
  8. customcrystallized from acetone

출처 및 근거

ORD 기록
ord-b11cbb3989ca4572a78c632b845a4b6a
출처 데이터셋
uspto-grants-1988_02
특허 번호
US04725610

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