Water → HCID 178443959, compound

HRID 1380357Notes

Reaction equation

HRID 1380357 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[CH3:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[C:11]=1[NH:17][S:18]([CH2:21][CH2:22][N:23]1[CH:27]=[CH:26][N:25]=[CH:24]1)(=[O:20])=[O:19].O>CN(C=O)C>[Br-:1].[CH3:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[C:11]=1[NH:17][S:18]([CH2:21][CH2:22][N+:23]1[CH:27]=[CH:26][N:25]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[CH:24]=1)(=[O:19])=[O:20]

Participants

5

Reactant 3

HCID 962WaterHCID 123691-BromoheptaneHCID 20188374HCID 20188374, compound

Product 1

HCID 178443959HCID 178443959, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Combine 3.46 g (0.019 mole) 1-bromoheptane and 5.16 g (0.018 mole) N-(2,6-dimethylphenyl)-2-[1H-imidazol-1-yl]ethane sulfonamide in 10 ml DMF and heat to 100° C. Follow progress of reaction by TLC on silica gel (acetonitrile:ammonium hydroxide, 9:1). After about 10 hours, allow reaction mixture to cool to room temperature. Pour the reaction mixture into 50 ml H2O and extract with 1×25 ml ether to give a white precipitate in the aqueous layer. Filter and recrystallize the precipitate from acetone to provide the title compound.

Workup

  1. customprogress of reaction by TLC on silica gel (acetonitrile:ammonium hydroxide, 9:1)
  2. customreaction mixture
  3. extractionextract with 1×25 ml ether
  4. customto give a white precipitate in the aqueous layer
  5. filtrationFilter
  6. customrecrystallize the precipitate from acetone

Sources & evidence

ORD record
ord-02a8c6cea5bc42ea8db36264d556ed34
Source dataset
uspto-grants-1986_04
Patent number
US04581370

Reaction notes

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