Bromoacetonitrile → Tosylacetonitrile

HRID 2061642

反応式

HRID 2061642 の反応式
Br[CH2:2][C:3]#[N:4].[CH3:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([O-:14])=[O:13])=[CH:8][CH:7]=1.[Na+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C1(C)C=CC=CC=1.CN(C)C=O>[C:6]1([CH3:5])[CH:11]=[CH:10][C:9]([S:12]([CH2:2][C:3]#[N:4])(=[O:14])=[O:13])=[CH:8][CH:7]=1

参加物

6

反応物 2

HCID 11534BromoacetonitrileHCID 2723791Sodium p-toluenesulfinate

生成物 1

HCID 79776Tosylacetonitrile収率 54%

試薬・触媒・溶媒 3

HCID 66133Benzyl triethylammonium chloride触媒HCID 1140Toluene溶媒HCID 6228Dimethylformamide溶媒

実験手順

3.37 g (28 mmol) of bromoacetonitrile and 640 mg (2.8 mmol) of benzyltriethylammonium chloride are added to a solution of 5 g (28 mmol) of sodium 4-methyl-benzenesulfinate in 50 ml of toluene and 50 ml of dimethylformamide. The reaction mixture is stirred at room temperature for 24 h. The heterogeneous mixture is filtered. The filtrate is evaporated and then purified on silica gel (heptane then heptane/ethyl acetate, 60/40 v/v). The product is triturated in heptane then filtered and dried. 2.95 g of (toluene-4-sulfonyl)-acetonitrile is obtained in the form of a pale yellow powder. (Yield=54%).

後処理

  1. filtrationThe heterogeneous mixture is filtered
  2. customThe filtrate is evaporated
  3. custompurified on silica gel (heptane
  4. customThe product is triturated in heptane
  5. filtrationthen filtered
  6. customdried

出典と根拠

ORDレコード
ord-d3bb4f395a0b4bfc9a3498c1b9d97497
出典データセット
uspto-grants-2012_10
特許番号
US08283378B2

関連ノート

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