Bromoacetonitrile → Tosylacetonitrile

HRID 2061642

반응식

HRID 2061642 반응식
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

참가 물질

6

반응물 2

HCID 11534BromoacetonitrileHCID 2723791Sodium p-toluenesulfinate

생성물 1

HCID 79776Tosylacetonitrile수율 54%

시약·촉매·용매 3

HCID 66133Benzyl triethylammonium chloride촉매HCID 1140Toluene용매HCID 6228Dimethylformamide용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-d3bb4f395a0b4bfc9a3498c1b9d97497
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08283378B2

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