Formaldehyde → 1-Hydroxymethyl-4-chloro-3-(2-nitro-3-chlorophenyl)pyrazole

HRID 342038Notes

Reaction equation

HRID 342038 reaction equation
N12CCCN=C1CCCC=C2.[Cl:12][C:13]1[C:14]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[C:19]=2[N+:25]([O-:27])=[O:26])=[N:15][NH:16][CH:17]=1.[CH2:28]=[O:29]>C1COCC1>[OH:29][CH2:28][N:16]1[CH:17]=[C:13]([Cl:12])[C:14]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[C:19]=2[N+:25]([O-:27])=[O:26])=[N:15]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 219795291,8-Diazabicyclo(5.4.0)undecen-7-eneHCID 178526739HCID 178526739, compound

Product 1

HCID 540890501-Hydroxymethyl-4-chloro-3-(2-nitro-3-chlorophenyl)pyrazoleYield 95.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.40 ml of 1,8-diazabicyclo[5.4.0]undecen-7-ene is added, at room temperature, to a solution of 7.0 g (0.027 mol) of 4-chloro-3-(2-nitro-3-chlorophenyl)pyrazole and 2.40 g of paraformaldehyde in 100 ml of THF. The reaction mixture is stirred for 4 hours at room temperature, concentrated under reduced pressure and taken up in a mixture of 150 ml of water and 150 ml of methylene chloride. The organic phase is dried over magnesium sulphate and concentrated under vacuum. 7.40 g of 1-hydroxymethyl-4-chloro-3-(2-nitro-3-chlorophenyl)pyrazole melting at 146° C. are obtained (yield: 95.5%).

Workup

  1. concentrationconcentrated under reduced pressure
  2. additiontaken up in a mixture of 150 ml of water and 150 ml of methylene chloride
  3. dry with materialThe organic phase is dried over magnesium sulphate
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-d0443ada79b84d609269cc0acfa6d6ac
Source dataset
uspto-grants-1999_01
Patent number
US05856514

Reaction notes

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