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Dimethylformamide → HCID 57736495, 화합물

HRID 1641752
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HRID 1641752 반응식
Br[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([CH:9]([S:19][C:20]2[CH:21]=[N:22][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:24][CH:25]=2)[C:10]2[C:15]([F:16])=[CH:14][CH:13]=[C:12]([F:17])[C:11]=2[F:18])=[CH:4][N:3]=1.C([Li])CCC.CN(C)[CH:37]=[O:38].[Cl-].[NH4+]>C1(C)C=CC=CC=1.O.ClCCl.CCCCCC>[CH3:8][C:6]1[C:5]([CH:9]([S:19][C:20]2[CH:21]=[N:22][C:23]([C:26]([F:27])([F:29])[F:28])=[CH:24][CH:25]=2)[C:10]2[C:15]([F:16])=[CH:14][CH:13]=[C:12]([F:17])[C:11]=2[F:18])=[CH:4][N:3]=[C:2]([CH:37]=[O:38])[CH:7]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

9

반응물 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 57736489HCID 57736489, 화합물HCID 178418339Butyllithium

생성물 1

HCID 57736495HCID 57736495, 화합물수율 59.1%

시약·촉매·용매 4

HCID 962Water용매
HCID 1140
Toluene
용매
HCID 6344Dichloromethane용매
HCID 8058Hexane용매

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온도
-40 °C

실험 절차

To a solution of 2-bromo-4-methyl-5-[[[6-(trifluoromethyl)pyridin-3-yl]thio](2,3,6-trifluorophenyl)methyl]pyridine (4.76 g, 9.65 mmol) in toluene (100 ml), a hexane solution of n-butyllithium (1.58 M, 6.72 ml, 10.6 mmol) was added in an argon atmosphere at −78° C. The reaction mixture was stirred for 30 minutes at −40° C., and then cooled again to −78° C., and N,N-dimethylformamide (0.897 ml, 11.6 mmol) was added. After completion of dropwise addition, the reaction mixture was allowed to warm to 0° C., and saturated aqueous ammonium chloride was added thereto at the same temperature. Dichloromethane and water were added to the reaction mixture, and the organic layer was separated. Subsequently, the organic layer was dried over anhydrous sodium sulfate and filtered, and then the filtrate was concentrated under reduced pressure. The resulting residue was subjected to flash silica gel chromatography, and the fraction obtained from an elution with hexane:ethyl acetate=5:1 was concentrated under reduced pressure, to obtain the title compound (2.52 g, 5.70 mmol, 59%) as a yellow oily substance.

후처리

  1. temperaturecooled again to −78° C.
  2. additionAfter completion of dropwise addition
  3. temperatureto warm to 0° C.
  4. customthe organic layer was separated
  5. dry with materialSubsequently, the organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customthe fraction obtained from an elution with hexane
  9. concentrationethyl acetate=5:1 was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-68d839063b11489997f3206ddff0eeaa
출처 데이터셋
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08114886B2

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