Potassium Hydroxide → HCID 66777200, compound

HRID 1616095Notes

Reaction equation

HRID 1616095 reaction equation
[OH-].[K+].OCS([O-])=O.[Na+].[NH2:9][C:10]1[C:11]([F:18])=[CH:12][C:13]([CH3:17])=[C:14]([SH:16])[CH:15]=1.[F:19][C:20]([F:24])([F:23])[CH2:21]I>CN(C=O)C.O>[F:19][C:20]([F:24])([F:23])[CH2:21][S:16][C:14]1[CH:15]=[C:10]([C:11]([F:18])=[CH:12][C:13]=1[CH3:17])[NH2:9]

Participants

7

Reactant 4

HCID 14797Potassium HydroxideHCID 677091,1,1-Trifluoro-2-iodoethaneHCID 23689980Sodium Formaldehyde SulfoxylateHCID 42629164HCID 42629164, compound

Product 1

HCID 66777200HCID 66777200, compoundYield 105.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of potassium hydroxide (78.5 g, 1.4 mol), sodium hydroxymethylsulfinate (Rongalite®, 74.4 g, 0.63 mol) and the crude 5-amino-4-fluoro-2-methyl-benzenethiol (110 g, 0.7 mol) in 380 mL of DMF was added dropwise 2,2,2-trifluoroethyl iodide (147.1 g, 0.704 mol). The reaction mixture was stirred for 2 hours at room temperature, poured into water and then extracted with ethyl acetate. The organic phase was dried with sodium sulfate and concentrated under reduced pressure to yield the title compound (176 g, 99%).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic phase was dried with sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7c9ce61c1e984726ab9d887c0b1d88e7
Source dataset
uspto-grants-2014_07
Patent number
US08765774B2

Reaction notes

Loading…