Dimethyl Sulfate → HCID 86745338, compound

HRID 1461647Notes

Reaction equation

HRID 1461647 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[NH:14][C:13](=[O:18])[CH2:12]3)[CH:5]=[C:4]([F:19])[C:3]=1[C:20]([F:23])([F:22])[F:21].[H-].[Na+].[CH3:26]OS(OC)(=O)=O>C1(C)C=CC=CC=1.C(OCC)(=O)C.O.CCCCCC>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[N:14]([CH3:26])[C:13](=[O:18])[CH2:12]3)[CH:5]=[C:4]([F:19])[C:3]=1[C:20]([F:23])([F:22])[F:21]

Participants

8

Reactant 3

HCID 6497Dimethyl SulfateHCID 24758Sodium hydride2×HCID 86745339HCID 86745339, compound

Product 1

HCID 86745338HCID 86745338, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 1140TolueneSolvent2×HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 5-[(2-chloro-α,α,α,6-tetrafluro-p-tolyl)oxy]-2-indolinone (16.8 g, 0.0485 mol) in toluene is treated in a single portion with a 60% sodium hydride dispersion in mineral oil (2.13 g, 0.0534 mol NaH) at 60° C., stirred for 30 minutes, treated dropwise with a solution of dimethylsulfate (5.1 mL, 0.0534 mol) in toluene over a 20 minute period at 60° C., stirred for 2 hours, cooled to room temperature and diluted with a mixture of ethyl acetate and water. The phases are separated, the organic phase is washed with brine and the aqueous phases are combined and further extracted with ethyl acetate. All organic phases are combined, dried over MgSO4, and concentrated in vacuo to give a light brown semi-solid residue. Trituration under a mixture of 3-5% ethyl acetate in hexane and filtration yields the title product as a light pink solid, 13.45 g (77%), mp 111-112° C.

Workup

  1. stirringstirred for 2 hours
  2. customThe phases are separated
  3. washthe organic phase is washed with brine
  4. extractionfurther extracted with ethyl acetate
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customto give a light brown semi-solid residue

Sources & evidence

ORD record
ord-0852f11dde444259869f76af32be5be2
Source dataset
uspto-grants-1991_12
Patent number
US05076835

Reaction notes

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