Water → HCID 86623646, compound

HRID 2080545Notes

Reaction equation

HRID 2080545 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([OH:11])[C:9]#[N:10].[C:12]1([CH3:22])[CH:17]=[CH:16][C:15]([S:18](Cl)(=[O:20])=[O:19])=[CH:14][CH:13]=1.CCN(CC)CC.O>C(#N)C>[CH3:22][C:12]1[CH:17]=[CH:16][C:15]([S:18]([O:11][CH:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])[C:9]#[N:10])(=[O:20])=[O:19])=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 98989362-(2-CHLOROPHENYL)-2-HYDROXYACETONITRILE

Product 1

HCID 86623646HCID 86623646, compoundYield 93.75%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-(2-chlorophenyl)-2-hydroxyacetonitrile (16.8 g, 0.1 mol) and 4-toluene sulfonyl chloride (21 g, 0.11 mol) was dissolved in acetonitrile (80 mL) in a suitable reaction flask, and Et3N (20 g, 0.2 mol) was added to the reaction dropwise at 0-25° C. Then the solution was stirred at room temperature for 5 h and afterwards refluxed until the reaction was completed by TLC monitoring. The acetonitrile was recovered and reaction mixture was diluted by water and extracted with butyl acetate. The organic layer was washed repeatedly with water and the butyl acetate was removed under reduced pressure giving the target product (30 g, yield 93.75%).

Workup

  1. temperatureafterwards refluxed until the reaction
  2. customThe acetonitrile was recovered
  3. customreaction mixture
  4. extractionextracted with butyl acetate
  5. washThe organic layer was washed repeatedly with water
  6. customthe butyl acetate was removed under reduced pressure

Sources & evidence

ORD record
ord-a1e1df8fd06d47ac9f6678b11af22c05
Source dataset
uspto-grants-2011_04
Patent number
US07932391B2

Reaction notes

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