Sodium hydride → HCID 58506482, compound

HRID 2167297Notes

Reaction equation

HRID 2167297 reaction equation
[OH:1][C:2]1[C:9]([OH:10])=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[H-].[Na+].CC1C=CC(S(O[CH2:24][CH2:25][O:26][CH2:27][CH2:28][O:29][CH3:30])(=O)=O)=CC=1>CS(C)=O>[OH:1][C:2]1[C:9]([O:10][CH2:24][CH2:25][O:26][CH2:27][CH2:28][O:29][CH3:30])=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 30178202,3-DihydroxybenzonitrileHCID 11076628HCID 11076628, compound

Product 1

HCID 58506482HCID 58506482, compoundYield 34.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
60 °C

Procedure

To a solution of 2,3-dihydroxybenzonitrile (13.5 g, 1 eq.) in DMSO (200 mL) was added NaH (60%, 8 g, 2eq.) and the resulting solution was stirred for 1 h at 60° C. 2-(2-Methoxyethoxy)ethyl 4-methylbenzenesulfonate (20 g, 0.7eq.) in DMSO (100 mL) was added dropwise at 60° C. and stirring was continued for another 1 h. The reaction was quenched by NH4Cl (sat.), the mixture was extracted with EtOAc (300 mL×3) and the combined organic layers were dried over Na2SO4. The solvent was evaporated and the residue was purified by silicon column (EtOAc/PE=1/1) to give the title compound (6 g, 25%).

Workup

  1. stirringstirring
  2. waitwas continued for another 1 h
  3. customThe reaction was quenched by NH4Cl (sat.)
  4. extractionthe mixture was extracted with EtOAc (300 mL×3)
  5. dry with materialthe combined organic layers were dried over Na2SO4
  6. customThe solvent was evaporated
  7. customthe residue was purified by silicon column (EtOAc/PE=1/1)

Sources & evidence

ORD record
ord-936ad2804655424898594371297763c0
Source dataset
uspto-grants-2015_06
Patent number
US09045440B2

Reaction notes

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