Acetic Acid → HCID 19086746, compound

HRID 1464579Notes

Reaction equation

HRID 1464579 reaction equation
[C:1](O)(=O)[CH3:2].[Cl:5][C:6]1[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[C:19]([F:27])[C:7]=1[O:8][C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[C:11]([N+:16]([O-:18])=[O:17])[CH:10]=1.C=O.[C-]#[N:31].[K+]>S(=O)(=O)(O)O.[Cl-].[Zn+2].[Cl-].O>[Cl:5][C:6]1[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[C:19]([F:27])[C:7]=1[O:8][C:9]1[CH:15]=[CH:14][C:12]([NH:13][CH2:2][C:1]#[N:31])=[C:11]([N+:16]([O-:18])=[O:17])[CH:10]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 9032Potassium CyanideHCID 19086749HCID 19086749, compound

Product 1

HCID 19086746HCID 19086746, compound

Reagents, catalysts & solvents 3

HCID 1118Sulfuric AcidCatalystHCID 3007855ZincchlorideCatalystHCID 962WaterSolvent

Procedure

Glacial acetic acid (40cm3) containing concentrated sulphuric acid (3 drops) was added to a stirred mixture of 4-(2-chloro-4-trifluoromethyl-6-fluorophenoxy)-2-nitroaniline (1 g), paraformaldehyde (0.26 g), anhydrous zinc chloride (1.43 g) and potassium cyanide (0.56 g). The resulting suspension was heated at 50°-55° C. for 7.5 hours and left to stand at room temperature overnight. The mixture was poured into water and extracted with ethyl acetate (×2). The combined organic phase was washed with water, dried (MgSO4), and filtered. The solvent was removed from the filtrate under vacuum to give 4-(2-chloro-4-trifluoromethyl-6-fluorophenoxy)-2-nitro-N-cyanomethylaniline (0.82 g) as an orange solid. M+ =389.

Workup

  1. temperatureThe resulting suspension was heated at 50°-55° C. for 7.5 hours
  2. waitleft
  3. extractionextracted with ethyl acetate (×2)
  4. washThe combined organic phase was washed with water
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customThe solvent was removed from the filtrate under vacuum

Sources & evidence

ORD record
ord-829e40cb308a48e5850f82d32ef6d4e2
Source dataset
uspto-grants-1994_04
Patent number
US05306692

Reaction notes

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