Dimethylformamide → HCID 178473095, 화합물

HRID 2270975노트

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HRID 2270975 반응식
[H-].[Na+].[CH2:3]([O:5][C:6](=[O:22])[C:7]([OH:21])=[CH:8][C:9]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([Cl:20])[CH:18]=2)[NH:13][CH:12]=1)=[O:10])[CH3:4].[C:23]1([S:29](Cl)(=[O:31])=[O:30])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.CN(C=O)C>C1COCC1>[CH2:3]([O:5][C:6](=[O:22])[C:7]([OH:21])=[CH:8][C:9]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([Cl:20])[CH:18]=2)[N:13]([S:29]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)(=[O:31])=[O:30])[CH:12]=1)=[O:10])[CH3:4]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 178473094HCID 178473094, 화합물

생성물 1

HCID 178473095HCID 178473095, 화합물수율 87%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a suspension of 0.88 g (22 mmol) of sodium hydride (60% dispersion in mineral oil) in THF (50 ml) was added under ice-cooling, 2.94 g (10 mmol) of 4-(5-chloroindol-3-yl)-2-hydroxy-4-oxo-2-butenoic acid ethyl ester prepared in Example 1 (1). After stirring for 15 min at room temperature, to the mixture was added dropwise a solution of 2.12 g (12 mmol) of benzenesulfonyl chloride in THF (20 ml). After stirring for 2 hours at room temperature, to the mixture was added DMF (8 ml). After stirring for additional 30 min, the reaction mixture was poured into ice-water containing 1N hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and then dried. The solvent was concentrated and the residue was crystallized from ether to give crude crystal, which was washed with ether to give 3.75 of the titled compound. Yield: 87%. Subsequent recrystallization from ethyl acetate afforded the pure ester, melted at. 156-157° C.

후처리

  1. additionwas added under ice-
  2. temperaturecooling
  3. stirringAfter stirring for 2 hours at room temperature, to the mixture
  4. stirringAfter stirring for additional 30 min
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with water and saturated brine
  7. customdried
  8. concentrationThe solvent was concentrated
  9. customthe residue was crystallized from ether
  10. customto give crude crystal, which
  11. washwas washed with ether

출처 및 근거

ORD 기록
ord-444fd7b4b33b4e3ea978fdb12ebd7829
출처 데이터셋
uspto-grants-2001_12
특허 번호
US06333323B1

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