Formaldehyde → 1-Acetoxymethyl-4-chloro-3-(3,5-dichlorophenyl)pyrazole

HRID 1586369Notes

Reaction equation

HRID 1586369 reaction equation
N12[CH2:11][CH2:10]CN=C1CCCC=C2.[Cl:12][C:13]1[C:14]([C:18]2[CH:23]=[C:22]([Cl:24])[CH:21]=[C:20]([Cl:25])[CH:19]=2)=[N:15][NH:16][CH:17]=1.C=[O:27].[C:28](Cl)(=[O:30])C>C1COCC1>[C:10]([O:30][CH2:28][N:16]1[CH:17]=[C:13]([Cl:12])[C:14]([C:18]2[CH:19]=[C:20]([Cl:25])[CH:21]=[C:22]([Cl:24])[CH:23]=2)=[N:15]1)(=[O:27])[CH3:11]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 6367Acetyl chlorideHCID 219795291,8-Diazabicyclo(5.4.0)undecen-7-eneHCID 178478181HCID 178478181, compound

Product 1

HCID 218526541-Acetoxymethyl-4-chloro-3-(3,5-dichlorophenyl)pyrazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

0.15 ml of 1,8-diazabicyclo(5.4.0)undecen-7-ene is added, at room temperature, to a solution of 2.55 g (0.01 mol) of 4-chloro-3-(3,5-dichlorophenyl)pyrazole and 0.90 g (0.030 mol) of paraformaldehyde in 70 ml of THF. The reaction mixture is stirred for 4 h at room temperature. A solution of 1.20 g (0.015 mol) of acetyl chloride in 10 ml of THF is run in dropwise at 0° C. and stirring is continued for 6 h at room temperature. The reaction mixture is concentrated to dryness. The residue is taken up in 15 ml of heptane and then dried. We obtain 3.05 g of 1-acetoxymethyl-4-chloro-3-(3,5-dichlorophenyl)pyrazole, melting at 95° C.

Workup

  1. customdropwise at 0° C.
  2. stirringstirring
  3. waitis continued for 6 h at room temperature
  4. concentrationThe reaction mixture is concentrated to dryness
  5. customdried

Sources & evidence

ORD record
ord-f00980d8259a4f7ea58a2fcd92c6eba4
Source dataset
uspto-grants-1999_08
Patent number
US05945382

Reaction notes

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