N,N-dimethyl-4-nitrosoaniline → HCID 88465577, compound

HRID 1614492Notes

Reaction equation

HRID 1614492 reaction equation
[Br-].[C:2]([C:4]1[CH:5]=[N:6][N:7]([C:16]2[C:21]([Cl:22])=[CH:20][C:19]([C:23]([F:26])([F:25])[F:24])=[CH:18][N:17]=2)[C:8]=1[CH2:9][N+]1C=CC=CC=1)#[N:3].[CH3:27][N:28]([CH3:37])[C:29]1[CH:34]=[CH:33][C:32]([N:35]=[O:36])=[CH:31][CH:30]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)C.O>[CH3:27][N:28]([CH3:37])[C:29]1[CH:34]=[CH:33][C:32]([N+:35]([O-:36])=[CH:9][C:8]2[N:7]([C:16]3[C:21]([Cl:22])=[CH:20][C:19]([C:23]([F:26])([F:25])[F:24])=[CH:18][N:17]=3)[N:6]=[CH:5][C:4]=2[C:2]#[N:3])=[CH:31][CH:30]=1

Participants

6

Reactant 3

HCID 8749N,N-dimethyl-4-nitrosoanilineHCID 11430Potassium CarbonateHCID 19790766HCID 19790766, compound

Product 1

HCID 88465577HCID 88465577, compoundYield 87.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirred suspension of 9.0 grams (0.020 mole) of 1-[[4-cyano-1-(3-chloro-5-trifluoromethylpyridin-2-yl)-1H-pyrazol-5-yl]methyl]pyridinium bromide and 3.5 grams (0.023 mole) of N,N-dimethyl-4-nitrosoaniline in 95 mL of ethanol was added a solution of 16 grams (0.12 mole) of potassium carbonate in 59 mL of water. When the addition was complete, the reaction mixture was stirred at ambient temperature for four hours. After this time, the reaction mixture was filtered. The filter cake was washed in succession with water, ethanol, and diethyl ether, yielding 7.6 grams of N-[4-(dimethylamino)phenyl]-a-[4-cyano-1-(3-chloro-5-trifluoromethylpyridin-2-yl)-1H-pyrazol-5-yl]nitrone. The nmr spectrum was consistent with the proposed structure.

Workup

  1. additionWhen the addition
  2. filtrationAfter this time, the reaction mixture was filtered
  3. washThe filter cake was washed in succession with water, ethanol, and diethyl ether

Sources & evidence

ORD record
ord-ab03eee1af5b4ec88f8c80742e75487c
Source dataset
uspto-grants-1993_03
Patent number
US05198014

Reaction notes

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