Hydrochloric Acid → HCID 14301772, compound

HRID 868304Notes

Reaction equation

HRID 868304 reaction equation
I[CH3:2].[OH-].[Na+].[Cl:5][C:6]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:7]=1[CH:15]([C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([C:25]([F:28])([F:27])[F:26])[CH:19]=1)[C:16]#[N:17].Cl>[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C.O1CCCC1>[Cl:24][C:21]1[CH:22]=[CH:23][C:18]([C:15]([C:7]2[CH:8]=[CH:9][C:10]([N+:12]([O-:14])=[O:13])=[CH:11][C:6]=2[Cl:5])([CH3:2])[C:16]#[N:17])=[CH:19][C:20]=1[C:25]([F:28])([F:26])[F:27]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodide2×HCID 14798Sodium HydroxideHCID 21288308HCID 21288308, compound

Product 1

HCID 14301772HCID 14301772, compoundYield 87.8%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred mixture of 14.2 parts of iodomethane, 153 parts of a sodium hydroxide solution 50%, 1 part of N,N,N-triethylbenzenemethanaminium chloride and 67.5 parts of tetrahydrofuran was added dropwise, during a period of 15 minutes, a solution of 37.5 parts of 2-chloro-α-[4-chloro-3-(trifluoromethyl)phenyl]-4-nitrobenzeneacetonitrile in 67.5 parts of tetrahydrofuran. The reaction mixture was stirred and heated for 4 hours at 50°-60° C. Another portion of 2.3 parts of iodomethane was added and the whole was stirred for 1 hour at 50° C. The mixture was poured into 1000 parts of crushed ice. The whole was acidified with concentrate hydrochloric acid. The product was extracted with trichloro-methane. The extract was dried, filtered and evaporated. The residue was stirred in 160 parts of ethanol. The product was filtered off, washed with 2,2'-oxybispropane and dried, yielding 34.2 parts (87.8%) of 4-chloro-α-(2-chloro-4-nitrophenyl)-α-methyl-3 -(trifluoromethyl)benzeneacetonitrile; mp. 162.5° C. (intermediate 17).

Workup

  1. additionwas added dropwise, during a period of 15 minutes
  2. temperatureheated for 4 hours at 50°-60° C
  3. stirringthe whole was stirred for 1 hour at 50° C
  4. additionThe mixture was poured into 1000 parts of crushed ice
  5. extractionThe product was extracted with trichloro-methane
  6. customThe extract was dried
  7. filtrationfiltered
  8. customevaporated
  9. stirringThe residue was stirred in 160 parts of ethanol
  10. filtrationThe product was filtered off
  11. washwashed with 2,2'-oxybispropane
  12. customdried

Sources & evidence

ORD record
ord-df128d91fe9343b5a0c64a34db3a548d
Source dataset
uspto-grants-1988_10
Patent number
US04778887

Reaction notes

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