Tosylacetonitrile → HCID 23047706, compound

HRID 2107137Notes

Reaction equation

HRID 2107137 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]Br)=[CH:4][CH:3]=1.[CH3:14][C:15]1[CH:20]=[CH:19][C:18]([S:21]([CH2:24][C:25]#[N:26])(=[O:23])=[O:22])=[CH:17][CH:16]=1.N12CCCN=C1CCCCC2>C1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:24]([S:21]([C:18]2[CH:19]=[CH:20][C:15]([CH3:14])=[CH:16][CH:17]=2)(=[O:23])=[O:22])[C:25]#[N:26])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 79776TosylacetonitrileHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 10753909HCID 10753909, compound

Product 1

HCID 23047706HCID 23047706, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 4.5 g (17.2 mmol) of 5-(4-chlorophenyl)pentyl bromide, 3.36 g (17.2 mmol) of (4-methylphenyl)sulfonylacetonitrile, 2.26 g (17.2 mmol) of 1,8-diazabicyclo(5,4,0)undec-7-ene and 30 ml of benzene is stirred at room temperature for 6 hours. Then the reaction mixture is washed with water; the organic phase is dried, and concentrated. The concentrate is chromatographed with a mixture of toluene and dioxane (10:1) on silica gel. Yield: 4.2 g (65% of theory) of the title compound, a colorless oil.

Workup

  1. washThen the reaction mixture is washed with water
  2. customthe organic phase is dried
  3. concentrationconcentrated
  4. customThe concentrate is chromatographed with a mixture of toluene and dioxane (10:1) on silica gel

Sources & evidence

ORD record
ord-9074b1b64ab44c1fabdba6ccab24ca47
Source dataset
uspto-grants-1990_06
Patent number
US04933367

Reaction notes

Loading…