N,N-Dimethylaniline → HCID 14719819, compound

HRID 1721940Notes

Reaction equation

HRID 1721940 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([O:9]CC=C)[CH:5]=[CH:4][C:3]=1[C:13]([C:15]1[N:19]([CH3:20])[N:18]=[CH:17][CH:16]=1)=[O:14].CN(C)[C:23]1[CH:28]=CC=C[CH:24]=1>CCOCC>[CH2:28]([C:5]1[C:6]([OH:9])=[C:7]([Cl:8])[C:2]([Cl:1])=[C:3]([C:13]([C:15]2[N:19]([CH3:20])[N:18]=[CH:17][CH:16]=2)=[O:14])[CH:4]=1)[CH:23]=[CH2:24]

Participants

4

Reactant 2

HCID 949N,N-DimethylanilineHCID 14622792HCID 14622792, compound

Product 1

HCID 14719819HCID 14719819, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
200 °C

Procedure

A suspension of 8.20 g of (2,3-dichloro-4-allyloxyphenyl)(1-methyl-5-pyrazolyl)methanone in N,N-dimethylaniline is stirred at 200° C. under argon gas atmosphere for 25 hours and cooled. The reaction mixture is diluted with ether and extracted with an aqueous 5% sodium hydroxide solution. The aqueous extract is washed with ether, adjusted to pH 5-6 with acetic acid and then extracted with chloroform. The organic layer is washed with water, dried and evaporated to give a solid, which is then purified by silica gel column chromatography to give 5.16 g of 6-allyl-2,3-dichloro-4-(1-methyl-5-pyrazolylcarbonyl)phenol.

Workup

  1. temperaturecooled
  2. extractionextracted with an aqueous 5% sodium hydroxide solution
  3. extractionThe aqueous extract
  4. washis washed with ether
  5. extractionextracted with chloroform
  6. washThe organic layer is washed with water
  7. customdried
  8. customevaporated
  9. customto give a solid, which
  10. customis then purified by silica gel column chromatography

Sources & evidence

ORD record
ord-42bf32de02db415db19d08296b7571e5
Source dataset
uspto-grants-1989_08
Patent number
US04853404

Reaction notes

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