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HCID 20144978, 화합물 → HCID 20145027, 화합물

HRID 648596
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HRID 648596 반응식
[CH3:1]C(C)([O-])C.[K+].[CH3:7][NH:8][C:9]1[S:10][C:11]([C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)=[C:12]([CH:14]=O)[N:13]=1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CS(C)=O>[CH3:7][NH:8][C:9]1[S:10][C:11]([C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)=[C:12]([CH:14]=[CH2:1])[N:13]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

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HCID 20144978HCID 20144978, 화합물HCID 23665647Potassium tert-butoxide

생성물 1

HCID 20145027HCID 20145027, 화합물수율 27.1%

시약·촉매·용매 2

HCID 74505Methyltriphenyliphosphonium bromide촉매HCID 679Dimethyl Sulfoxide용매

실험 절차

Potassium tert-butoxide (1.46 g) was added to a solution of 2-methylamino-5-(4-pyridyl)-4-thiazolecarbaldehyde (1.9 g) and methyltriphenylphosphonium bromide (4.66 g) in dimethyl sulfoxide (87 ml) and the mixture was stirred for 5 hours at ambient temperature. The reaction mixture was poured into ice-water (300 ml) and extracted with ethyl acetate (100 ml×2). The extract was washed with a saturated aqueous solution of sodium chloride (100 ml) and dried over magnesium sulfate. Solvent was distilled off and the residue was subjected to column chromatography on silica gel (120 g) and eluted with a mixture of chloroform and methanol (40:1). The fractions containing the object compound were combined and concentrated until the volume was about 15 ml. The resultant white needles were collected by filtration and washed with cold ethyl acetate and dried under reduced pressure to give white needles of 2-methylamino-5-(4-pyridyl)-4-vinylthiazole (510 mg).

후처리

  1. extractionextracted with ethyl acetate (100 ml×2)
  2. washThe extract was washed with a saturated aqueous solution of sodium chloride (100 ml)
  3. dry with materialdried over magnesium sulfate
  4. distillationSolvent was distilled off
  5. washeluted with a mixture of chloroform and methanol (40:1)
  6. additionThe fractions containing the object compound
  7. concentrationconcentrated until the volume
  8. filtrationThe resultant white needles were collected by filtration
  9. washwashed with cold ethyl acetate
  10. customdried under reduced pressure

출처 및 근거

ORD 기록
ord-1082431640054c78b2700504828866f8
출처 데이터셋
uspto-grants-1988_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04735957

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