Pivaloyl chloride → HCID 178429852, compound

HRID 2245382Notes

Reaction equation

HRID 2245382 reaction equation
[CH2:1]=[C:2]1[S:6][C:5](=[NH:7])[N:4]([C:8]2[CH:21]=[CH:20][C:11]3[O:12][C:13]([F:19])([F:18])[C:14]([F:17])([F:16])[O:15][C:10]=3[CH:9]=2)[CH2:3]1.CCN(C(C)C)C(C)C.[C:31](Cl)(=[O:36])[C:32]([CH3:35])([CH3:34])[CH3:33]>C(#N)C.C(Cl)Cl>[CH3:33][C:32]([CH3:35])([CH3:34])[C:31](/[N:7]=[C:5]1\[S:6][C:2]([CH3:1])=[CH:3][N:4]\1[C:8]1[CH:21]=[CH:20][C:11]2[O:12][C:13]([F:19])([F:18])[C:14]([F:16])([F:17])[O:15][C:10]=2[CH:9]=1)=[O:36]

Participants

6

Reactant 3

HCID 62493Pivaloyl chloride2×HCID 81531DiisopropylethylamineHCID 866191675-Methylene-3-(2,2,3,3-tetrafluoro-2,3-dihydrobenzo[b][1,4]dioxin-6-yl)thiazolidin-2-imine

Product 1

HCID 178429852HCID 178429852, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 5-methylene-3-(2,2,3,3-tetrafluoro-2,3-dihydrobenzo[b][1,4]dioxin-6-yl)thiazolidin-2-imine (Example 22C, 0.14 g, 0.44 mmol) in acetonitrile (3 mL) was added Hunig's base (0.062 g, 0.48 mmol) followed by pivaloyl chloride (0.064 g, 0.54 mmol). The mixture was heated for 12 hours at 65° C. The mixture was cooled down and more pivaloyl chloride (0.064 g, 0.54 mmol) was added. The mixture was heated again at 65° C. for 12 hours. After cooling, the reaction mixture was diluted with CH2Cl2 (50 mL) and washed with water and brine. The organic phase was dried over sodium sulfate, filtered and dried. After evaporation under reduced pressure, the residue was chromatographed over silica using CH2Cl2-5%MeOH/CH2Cl2 to supply the titled compound. 1H NMR (CDCl3) δ ppm 1.05 (9H), 2.30 (3H), 6.80 (1H), 7.20 (1H), 7.40 (1H), 7.50 (1H); MS (ESI) m/z 405 (M+H)+.

Workup

  1. temperatureThe mixture was cooled down
  2. temperatureThe mixture was heated again at 65° C. for 12 hours
  3. temperatureAfter cooling
  4. washwashed with water and brine
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. filtrationfiltered
  7. customdried
  8. customAfter evaporation under reduced pressure
  9. customthe residue was chromatographed over silica

Sources & evidence

ORD record
ord-5fecc9fa95d84400aa43a112d704bdde
Source dataset
uspto-grants-2010_03
Patent number
US07683084B2

Reaction notes

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