Hydrochloric Acid → Fenpiclonil

HRID 2118833Notes

Reaction equation

HRID 2118833 reaction equation
[OH-].[K+].[C:3]([C:5](=[CH:9][C:10]1[CH:15]=[CH:14][CH:13]=C(Cl)[C:11]=1[Cl:17])[C:6](O)=O)#[N:4].S([CH2:28][N+:29]#[C-])(C1C=CC(C)=CC=1)(=O)=O.Cl.[CH2:32]([Cl:34])Cl>CO.O>[Cl:17][C:11]1[C:32]([Cl:34])=[CH:13][CH:14]=[CH:15][C:10]=1[C:9]1[C:5]([C:3]#[N:4])=[CH:6][NH:29][CH:28]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 14797Potassium HydroxideHCID 161915Tosylmethyl isocyanideHCID 544369512-Cyano-3-(2,3-dichlorophenyl)prop-2-enoic acid

Product 1

HCID 91724FenpiclonilYield 99%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

12.62 g (225.0 m mol) of potassium hydroxide was dissolved in 80 ml of methanol. While being cooled at a temperature 0° to 10° C., the solution was fed with 12.10 g (50.0 m mol) of alpha-cyano-2,3-dichlorocinnamic acid and the mixture was stirred for 20 min. in the same temperature range. A solution of 10.25 g (52.5 m mol) of tosyl methylisocyanide in 70 ml of methylene chloride was added dropwise, at a temperature from 0° to 5° C., to the above mixture. The reaction mixture was then stirred for 30 min. at the same temperature to complete the reaction. Then, to the reaction mixture 50 ml of water was added and was neutralized to pH 8 by 10% HCl. From the neutralized mixture, methylene chloride and methanol was distilled off under reduced pressure, then, 100 ml of water was further added thereto and the mixture was stirred for 30 min. to precipitate crystals. The crystals were filtered off and washed with water and dried. 11.73 g of 3-(2,3-dichlorophenyl)-4-cyanopyrrole was obtained. Yield 99.0%, Melting point 152°-153° C.

Workup

  1. temperatureWhile being cooled at a temperature 0° to 10° C.
  2. stirringThe reaction mixture was then stirred for 30 min. at the same temperature
  3. customthe reaction
  4. distillationFrom the neutralized mixture, methylene chloride and methanol was distilled off under reduced pressure
  5. addition100 ml of water was further added
  6. stirringthe mixture was stirred for 30 min.
  7. customto precipitate crystals
  8. filtrationThe crystals were filtered off
  9. washwashed with water
  10. customdried

Sources & evidence

ORD record
ord-279e78a4a43d469285f776a5266eaeb1
Source dataset
uspto-grants-1987_07
Patent number
US04680413

Reaction notes

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