Water → HCID 14653376, compound

HRID 2352236Notes

Reaction equation

HRID 2352236 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:12]=[C:13]([F:15])[CH:14]=1)[CH2:5][N:6]1[CH2:10][CH2:9][N:8]=[C:7]1[SH:11].[OH-].[K+].O.[CH3:19][O:20][C:21](=[O:25])[CH2:22][CH2:23]Br>CN(C)C=O>[C:21]([CH2:22][CH2:23][S:11][C:7]1[N:6]([CH2:5][C:4]2[CH:3]=[C:2]([F:1])[CH:14]=[C:13]([F:15])[CH:12]=2)[CH2:10][CH2:9][N:8]=1)([O:20][CH3:19])=[O:25]

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 76934Methyl 3-bromopropanoateHCID 178505925HCID 178505925, compound

Product 1

HCID 14653376HCID 14653376, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
95 °C

Procedure

1-(3,5-difluorobenzyl)-2-mercaptoimidazoline, prepared as in example 8, and potassium hydroxide in equimolar proportions in dimethylformamide and water are stirred under argon at ambient temperature, and one mole of methyl-3-bromopropionate is added. The reaction mixture is heated at 95° C. overnight, cooled, and extracted three times with ether, and the combined ether extracts are concentrated. Purification by flash chromatography on silica gel gives 2-(2-carbomethoxyethylthio)-1-(3,5-difluorobenzyl)imidazoline.

Workup

  1. temperaturecooled
  2. extractionextracted three times with ether
  3. concentrationthe combined ether extracts are concentrated
  4. customPurification by flash chromatography on silica gel

Sources & evidence

ORD record
ord-e96c27d363f44a50ac2af30bb05486e9
Source dataset
uspto-grants-1989_10
Patent number
US04876266

Reaction notes

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