Water → HCID 53646179, compound

HRID 1276089Notes

Reaction equation

HRID 1276089 reaction equation
[H-].[Na+].[Cl:3][C:4]1[C:5]([C:14]2[CH:22]=[CH:21][C:17]3[NH:18][N:19]=[N:20][C:16]=3[CH:15]=2)=[N:6][CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1.Br[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26].O>CN(C)C=O>[Cl:3][C:4]1[C:5]([C:14]2[CH:22]=[CH:21][C:17]3[N:18]([CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[N:19]=[N:20][C:16]=3[CH:15]=2)=[N:6][CH:7]=[C:8]([C:10]([F:11])([F:12])[F:13])[CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 178506242HCID 178506242, compound

Product 1

HCID 53646179HCID 53646179, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

0.5 g of sodium hydride (80% strength by weight suspension in mineral oil) in 25 ml of anhydrous dimethylformamide was treated dropwise with a solution of 4.4 g of 5-(3-chloro-5-trifluoromethylpyridin-2-yl)benzotriazole in 25 ml of dimethylformamide. After stirring for 15 min, 2.6 g of ethyl bromoacetate were added dropwise, after which the mixture was stirred at 23° C. for 20 hours. The batch was then poured into 200 ml of water. After extracting three times with 100 ml of tert-butyl methyl ether each time, the combined organic phases were washed with 100 ml of water, dried over sodium sulfate and concentrated. The oil residue was purified by means of chromatography on silica gel (eluent: cyclohexane/ethyl acetate=6:1). The following were eluted in succession (without taking into account mixed fractions): 1.0 g of 5-(3-chloro-5-trifluoromethylpyridin-2yl)-2-ethoxycarbonylmethylbenzotriazole; m.p.: 127-129° C.

Workup

  1. stirringafter which the mixture was stirred at 23° C. for 20 hours
  2. extractionAfter extracting three times with 100 ml of tert-butyl methyl ether each time
  3. washthe combined organic phases were washed with 100 ml of water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe oil residue was purified by means of chromatography on silica gel (eluent: cyclohexane/ethyl acetate=6:1)
  7. washThe following were eluted in succession (without taking into account mixed fractions)

Sources & evidence

ORD record
ord-46cbb0a6e16e46fcb3b3823953f15cd2
Source dataset
uspto-grants-2000_12
Patent number
US06165941

Reaction notes

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