1,1-Dimethylhydrazine → HCID 18696625, compound

HRID 1870555Notes

Reaction equation

HRID 1870555 reaction equation
[N:1]([C:4]1[C:5]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:12]=2)=[N:6][CH:7]=[CH:8][CH:9]=1)=[C:2]=[O:3].C[N:25]([CH3:27])[NH2:26].[Cl:28][C:29](Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl>O1CCCC1.C(Cl)Cl>[Cl:28][C:29]1[N:1]([C:4]2[C:5]([O:10][C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([O:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[CH:12]=3)=[N:6][CH:7]=[CH:8][CH:9]=2)[C:2](=[O:3])[N:25]([CH3:27])[N:26]=1

Participants

6

Reactant 3

HCID 59761,1-DimethylhydrazineHCID 94429TriphosgeneHCID 186966243-Isocyanato-2-(3-phenoxyphenoxy)pyridine

Product 1

HCID 18696625HCID 18696625, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

The solids from Step B were dissolved in 100 mL of dry tetrahydrofuran. 1,1-Dimethylhydrazine (3 g, 50.0 mmol) was added and the reaction mixture was stirred at room temperature for 16 h. The reaction mixture was concentrated under reduced pressure. The residue was diluted with water and extracted twice with diethyl ether. The combined organic layers were then washed once with saturated aqueous NaCl solution and dried over magnesium sulfate. The solvent was removed under reduced pressure to give an oil. This oil was then dissolved in 200 mL methylene chloride and cooled to 0° C. at which temperature triphosgene (4.08 g, 13.7 mmol) was added. The reaction mixture was refluxed for 16 h, cooled to room temperature and washed once with water. The organic layer was then dried over magnesium sulfate and concentrated under reduced pressure to yield a crude oil which was purified by silica gel chromatography using 3:2/hexanes:ethyl acetate as the eluent to yield 2 g of the title compound of Step C, a compound of the invention, as a solid. 1H NMR (CDCl3 ; 300 MHz): δ 3.53 (s,3H), 6.8-6.9 (m,3H), 7.0-7.2 (m,4H), 7.3-7.4 (m,3H), 7.71 (dd,1H, J=1.9, 7.7 Hz), 8.27 (dd,1H, J=1.8, 4.9 Hz).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionThe residue was diluted with water
  3. extractionextracted twice with diethyl ether
  4. washThe combined organic layers were then washed once with saturated aqueous NaCl solution
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customto give an oil
  8. additionwas added
  9. temperatureThe reaction mixture was refluxed for 16 h
  10. temperaturecooled to room temperature
  11. washwashed once with water
  12. dry with materialThe organic layer was then dried over magnesium sulfate
  13. concentrationconcentrated under reduced pressure
  14. customto yield a crude oil which
  15. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-19b46df86edf4634bd8976bf26fd6351
Source dataset
uspto-grants-2000_08
Patent number
US06096895

Reaction notes

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