Propargyl bromide → HCID 22114852, compound

HRID 1276076Notes

Reaction equation

HRID 1276076 reaction equation
[Cl:1][C:2]1[C:3]([C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([NH:19][C:20](=[O:23])[CH2:21]Cl)[CH:13]=2)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[H-].[Na+].[CH2:26](Br)[C:27]#[CH:28]>CN(C)C=O>[Cl:1][C:2]1[C:3]([C:12]2[CH:17]=[CH:16][C:15]3[O:18][CH2:21][C:20](=[O:23])[N:19]([CH2:28][C:27]#[CH:26])[C:14]=3[CH:13]=2)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 24758Sodium hydrideHCID 135618682HCID 135618682, compound

Product 1

HCID 22114852HCID 22114852, compoundYield 47.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
20 °C

Procedure

A solution of 3.6 g (11.0 mmol) of 3-chloro-2-[3-(2-chloroacetylamino)-4-hydroxyphenyl]-5-trifluoromethylpyridine in 50 ml of anhydrous dimethylformamide was added dropwise at 0° C. to a suspension of 0.4 g (12 mmol) of sodium hydride (80% strength in mineral oil) which had been freed of mineral oil and 50 ml of anhydrous dimethylformamide. After stirring for 15 minutes, 1.3 g (11.0 mmol) of propargyl bromide were added dropwise to this mixture. The reaction mixture was then slowly allowed to warm to about 20° C. room temperature, stirred for a further three hours and then poured into 500 ml of ice water. The aqueous phase was extracted three times with 200 ml of ethyl acetate each time. The combined organic phases were washed twice with a little water, dried over sodium sulfate and then concetrated. Chromatographic purification of the residure on silica gel (eluent: cyclohexane/ethyl acetate 4:1) gave 1.9 g (47%) of colorless crystals of m.p.: 136-137° C.

Workup

  1. stirringstirred for a further three hours
  2. extractionThe aqueous phase was extracted three times with 200 ml of ethyl acetate each time
  3. washThe combined organic phases were washed twice with a little water
  4. dry with materialdried over sodium sulfate
  5. customChromatographic purification of the residure on silica gel (eluent: cyclohexane/ethyl acetate 4:1)

Sources & evidence

ORD record
ord-44cbdd37b54642829189c7357fecc1ba
Source dataset
uspto-grants-2000_12
Patent number
US06165941

Reaction notes

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