4-Toluenesulfonyl chloride → 2-(5-Bromo-2-pyridinylamino)-1-cyanoethyl toluene-4-sulfonate

HRID 1792457ノート

反応式

HRID 1792457 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][CH2:9][CH:10]([OH:13])[C:11]#[N:12])=[N:6][CH:7]=1.C(N(C(C)C)CC)(C)C.[C:23]1([CH3:33])[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1.C(=O)(O)[O-].[Na+]>ClCCl>[C:23]1([CH3:33])[CH:28]=[CH:27][C:26]([S:29]([O:13][CH:10]([C:11]#[N:12])[CH2:9][NH:8][C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][N:6]=2)(=[O:31])=[O:30])=[CH:25][CH:24]=1

参加物

6

反応物 4

HCID 73974-Toluenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 220313423-(5-Bromo-2-pyridinylamino)-2-hydroxypropionitrile

生成物 1

HCID 235374122-(5-Bromo-2-pyridinylamino)-1-cyanoethyl toluene-4-sulfonate収率 64.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

7.2 g of 3-(5-bromo-2-pyridinylamino)-2-hydroxypropionitrile was dissolved in 60 mL dichloromethane, and 7.8 mL diisopropyl ethylamine and 6.3 g of 4-toluenesulfonic acid chloride were added thereto, and while the temperature of the mixture was gradually increased to room temperature, the mixture was stirred for 2 hours. An aqueous saturated sodium bicarbonate solution was poured into the reaction mixture which was then extracted with ethyl acetate and washed with brine, then the organic layer was dried over anhydrous sodium sulfate, the solvent was removed, and the resulting crude product was purified by silica gel column chromatography (ethyl acetate/hexane) to give 7.64 g of the title compound (yellow oil).

後処理

  1. extractionwas then extracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  4. customthe solvent was removed
  5. customthe resulting crude product was purified by silica gel column chromatography (ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-0dbdc9783d4d489ab198e2f789e8084b
出典データセット
uspto-grants-2006_07
特許番号
US07074801B1

反応ノート

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