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Dimethylformamide → HCID 57736495、化合物

HRID 1641752
ノート
印刷プレビュー

反応式

HRID 1641752 の反応式
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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

9

反応物 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 57736489HCID 57736489、化合物HCID 178418339Butyllithium

生成物 1

HCID 57736495HCID 57736495、化合物収率 59.1%

試薬・触媒・溶媒 4

HCID 962Water溶媒
HCID 1140
Toluene
溶媒
HCID 6344Dichloromethane溶媒
HCID 8058Hexane溶媒

反応条件

温度
-40 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-68d839063b11489997f3206ddff0eeaa
出典データセット
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08114886B2

反応ノート

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