Potassium Carbonate → HCID 66684791, compound

HRID 1048974Notes

Reaction equation

HRID 1048974 reaction equation
F[C:2]1[CH:7]=[C:6](F)[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].C([O-])([O-])=O.[K+].[K+].[N:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][NH2:25])[CH:19]=1.[CH3:26][S-:27].[Na+]>CS(C)=O>[CH3:26][S:27][C:6]1[CH:5]=[CH:4][C:3]([N+:9]([O-:11])=[O:10])=[C:2]([CH:7]=1)[NH:25][CH2:24][C:20]1[CH:19]=[N:18][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 310183-PyridinemethanamineHCID 679672,4-Difluoronitrobenzene2×HCID 4378561Sodium methanethiolate

Product 1

HCID 66684791HCID 66684791, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a stirred solution of 2,4-difluoro-1-nitrobenzene (2 g, 0.012 mol) in DMSO (60 ml) was added K2CO3 (5.2 g, 0.037 mol). Then pyridin-3-ylmethanamine (1.05 g, 0.013 mol) was added drop wise and the resulting solution was continued to stir at room temperature for 6 h. After complete conversion of 2,4-difluoro-1-nitrobenzene monitored by MS sodium thio-methoxide (1.2 g, 0.013 mol) was added and heated at 60° C. for the next 12 h. The reaction was diluted with ice cold water and extracted with ethyl acetate (3×100 ml). The combined organic layers were washed with brine dried over Na2SO4 and concentrated under vacuum to afford the crude compound which was purified by chromatography to obtain title compound 5-(methyl-thio)-2-nitro-N-(pyridin-3-ylmethyl)aniline as a yellow solid. 1H NMR (400 MHz, CDCl3), δ: 8.65 (s, 1H), 8.58 (s, 2H), 8.11-8.09 (d, J=9.2 Hz, 1H), 7.69-7.67 (d, J=7.6 Hz, 1H), 7.33-7.29 (m, 1H), 6.54-6.51 (dd, J=7.2 Hz, J=1.6 Hz, 1H), 6.43 (s, 1H), 4.58-4.57 (d, J=5.6 Hz, 2H), 2.48 (s, 3H). MS (M+1): 276.

Workup

  1. additionwas added
  2. temperatureheated at 60° C. for the next 12 h
  3. additionThe reaction was diluted with ice cold water
  4. extractionextracted with ethyl acetate (3×100 ml)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under vacuum
  8. customto afford the crude compound which
  9. customwas purified by chromatography

Sources & evidence

ORD record
ord-142103a776e444e7a6e2df96f41d4400
Source dataset
uspto-grants-2016_07
Patent number
US09382226B2

Reaction notes

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