Allyl bromide → HCID 15118087, compound

HRID 476521Notes

Reaction equation

HRID 476521 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:4]=[C:5]([CH:15]=[CH:16][CH:17]=1)[CH2:6][S:7]([NH:10][CH2:11][C:12]([NH2:14])=[O:13])(=[O:9])=[O:8].[H-].[Na+].[CH2:22](Br)[CH:23]=[CH2:24]>CN(C)C=O.O>[CH2:24]([N:10]([CH2:11][C:12]([NH2:14])=[O:13])[S:7]([CH2:6][C:5]1[CH:15]=[CH:16][CH:17]=[C:3]([C:2]([F:18])([F:1])[F:19])[CH:4]=1)(=[O:9])=[O:8])[CH:23]=[CH2:22]

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 14517965HCID 14517965, compound

Product 1

HCID 15118087HCID 15118087, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

2.96 g of 3-trifluoromethylbenzylsulfonamidoacetamide was dissolved in 10 ml of dry dimethylformamide. To this ice-cooled solution was added 0.24 g of sodium hydride. The reaction mixture was stirred for 15 minutes at room temperature and then 0.95 ml of allyl bromide dissolved in 5 ml of dimethylformamide was added dropwise. Reaction was essentially instantaneous. After about 30 minutes, the reaction mixture was diluted with 150 ml of water and extracted twice with 75 ml portions of diethyl ether. Petroleum ether was added to the combined ether phases until cloudiness occurred, and this solution was washed with 100 ml of water. The organic phase was dried over magnesium sulfate and stripped to a white solid. Trituration with carbon tetrachloride afforded 2.8 g of the title compound, m.p. 91° to 92° C.

Workup

  1. additionwas added dropwise
  2. customReaction
  3. waitAfter about 30 minutes
  4. extractionextracted twice with 75 ml portions of diethyl ether
  5. additionPetroleum ether was added to the combined ether phases until cloudiness
  6. washthis solution was washed with 100 ml of water
  7. dry with materialThe organic phase was dried over magnesium sulfate

Sources & evidence

ORD record
ord-f2c11115831f4cdf8917c6f32db3da9f
Source dataset
uspto-grants-1989_12
Patent number
US04885027

Reaction notes

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