Hydrochloric Acid → HCID 19785567, compound

HRID 256774Notes

Reaction equation

HRID 256774 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH:8]([C:10]2[N:11]=[C:12]([NH:20][CH3:21])[S:13][C:14]=2[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH3:9])[CH:5]=[CH:4][C:3]=1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[CH3:28]I.[OH-].[Na+].Cl>C1C=CC=CC=1.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O>[F:1][C:2]1[CH:7]=[C:6]([CH:8]([C:10]2[N:11]=[C:12]([N:20]([CH3:28])[CH3:21])[S:13][C:14]=2[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH3:9])[CH:5]=[CH:4][C:3]=1[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 19785549HCID 19785549, compound

Product 1

HCID 19785567HCID 19785567, compoundYield 100%

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

To a solution of ethyl 4-(1-(2-fluoro-4-biphenylyl)-ethyl)-2-methylamino-5-thiazolecarboxylate (3.55 g, 9.23 mmoles) and methyl iodide (2.81 g, 18.8 mmoles) in benzene (70 ml) were added 50% aqueous solution of sodium hydroxide (35 ml) and tetra-n-butylammonium hydrogen sulfate (3.13 g, 9.22 mmoles) and the resulting mixture was stirred at room temperature for 5.5 hours. The reaction mixture was diluted with water, acidified to pH 6 with 1M hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and concentrated under reduced pressure. Purification of the residue by means of silica gel column gave the desired ethyl 4-(1-(2-fluoro-4-biphenylyl)ethyl)-2-dimethylamino-5-thiazolecarboxylate (3.68 g, 9.23 mmoles, quantitative yield) as a colorless oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customPurification of the residue by means of silica gel column

Sources & evidence

ORD record
ord-ce303a92e1774a0f9696cc44790655c0
Source dataset
uspto-grants-1993_11
Patent number
US05258396

Reaction notes

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