Triethylamine → 4-(2-Fluoro-4-nitrophenyl)thiomorpholine

HRID 56094Notes

Reaction equation

HRID 56094 reaction equation
[NH:1]1[CH2:6][CH2:5][S:4][CH2:3][CH2:2]1.CCN(CC)CC.[F:14][C:15]1[CH:16]=[C:17]([N+:22]([O-:24])=[O:23])[CH:18]=[CH:19][C:20]=1F>CCOC(C)=O>[F:14][C:15]1[CH:16]=[C:17]([N+:22]([O-:24])=[O:23])[CH:18]=[CH:19][C:20]=1[N:1]1[CH2:6][CH2:5][S:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 67164ThiomorpholineHCID 1230531,2-Difluoro-4-nitrobenzene

Product 1

HCID 108240714-(2-Fluoro-4-nitrophenyl)thiomorpholineYield 72.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of thiomorpholine (3.57 g, 34.56 mmol) and Et3N (3.50 g, 34.56 mmol) in EtOAc was added 3,4-difluoronitrobenzene (5.00 g, 31.43 mmol) dropwise over a period of 30 min in an ice bath. Upon the end of addition the reaction mixture was warmed to rt slowly, and solid was precipitated out. The mixture was filtered. The filter cake was washed with an appropriate amount of water, dried in vacuo to obtain the 1st crop of product. The filtrate was extracted with EtOAc. The combined organic phases were dried over anhydrous Na2SO4 and concentrated in vacuo to obtain the 2nd crop of product. The solids of 1st crop and 2nd crop were combined to give the title compound as a yellow solid (5.50 g, 72%).

Workup

  1. additionUpon the end of addition the reaction mixture
  2. customsolid was precipitated out
  3. filtrationThe mixture was filtered
  4. washThe filter cake was washed with an appropriate amount of water
  5. customdried in vacuo
  6. customto obtain the 1st crop of product
  7. extractionThe filtrate was extracted with EtOAc
  8. dry with materialThe combined organic phases were dried over anhydrous Na2SO4
  9. concentrationconcentrated in vacuo
  10. customto obtain the 2nd crop of product

Sources & evidence

ORD record
ord-198e6cfb0c8c40b490dbd50204ff5491
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Reaction notes

Loading…