Hydrochloric Acid → HCID 86623646, compound

HRID 2080547Notes

Reaction equation

HRID 2080547 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@H: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.CN(C)C1C=CC=CC=1.Cl>C(OCCCC)(=O)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 313Hydrochloric AcidHCID 949N,N-DimethylanilineHCID 73974-Toluenesulfonyl chlorideHCID 11030217HCID 11030217, compound

Product 1

HCID 86623646HCID 86623646, compoundYield 96.9%

Reagents, catalysts & solvents 1

HCID 31272Butyl AcetateSolvent

Procedure

(s)-2-(2-chlorophenyl)-2-hydroxyacetonitrile (16.8 g, 0.1 mol) and 4-toluene sulfonyl chloride (21 g, 0.11 mol) was dissolved in butyl acetate (100 mL) in a suitable reaction flask. N,N-dimethyl aniline (10 mL) was added dropwise to the mixture at 0-5° C. and the reaction continued at 20-25° C. for 3 hours, and then refluxed till the reaction was completed by TLC monitoring. Cold down the reaction mixture, 5% HCl (50 mL) was added and stirred at room temperature. Butyl acetate layer was separated and washed with water (50 ml×2). After removal of the solvent under reduced pressure, the target product was obtained (31 g, yield 96.9%).

Workup

  1. temperaturerefluxed till the reaction
  2. customButyl acetate layer was separated
  3. washwashed with water (50 ml×2)
  4. customAfter removal of the solvent under reduced pressure
  5. customthe target product was obtained (31 g, yield 96.9%)

Sources & evidence

ORD record
ord-c9078f5cb8df4f41b6405799b183a1bd
Source dataset
uspto-grants-2011_04
Patent number
US07932391B2

Reaction notes

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