3-Chloro-1-propanol → 3-((4-Fluorophenyl)(thiazol-2-yl)amino)propan-1-ol

HRID 2267398Notes

Reaction equation

HRID 2267398 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[S:10][CH:11]=[CH:12][N:13]=2)=[CH:4][CH:3]=1.Cl[CH2:15][CH2:16][CH2:17][OH:18]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1.[OH-].[Na+].CCOC(C)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([C:9]2[S:10][CH:11]=[CH:12][N:13]=2)[CH2:15][CH2:16][CH2:17][OH:18])=[CH:6][CH:7]=1

Participants

7

Reactant 2

HCID 123133-Chloro-1-propanolHCID 25093329N-(4-Fluorophenyl)thiazol-2-amine

Product 1

HCID 574288463-((4-Fluorophenyl)(thiazol-2-yl)amino)propan-1-ol

Reagents, catalysts & solvents 4

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of N-(4-fluorophenyl)thiazol-2-amine (6.00 g, 30.0 mmol), 3-chloropropanol (3.87 mL, 46.4 mmol), tetra-n-butylammonium hydrogensulfate (1.05 g, 3.09 mmol) in toluene (100 mL) and NaOH (40% w/v in water)(20 mL) was refluxed for 3 h. On cooling, the reaction mixture was diluted with EtOAc (100 mL), washed with water (4×100 mL), brine (100 mL), dried over anhydrous sodium sulphate, filtered and concentrated in vacuo. The crude product was purified by flash chromatography with 50-80% EtOAc in hexane to afford the title compound as a brown oil, 3.287 g. MS (M+H)+ 253.

Workup

  1. temperaturewas refluxed for 3 h
  2. temperatureOn cooling
  3. washwashed with water (4×100 mL), brine (100 mL)
  4. dry with materialdried over anhydrous sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by flash chromatography with 50-80% EtOAc in hexane

Sources & evidence

ORD record
ord-ef42acc6dff54ed8813c6d673aeeeb4c
Source dataset
uspto-grants-2010_12
Patent number
US07858785B2

Reaction notes

Loading…