Diazomethane → HCID 23333415, compound

HRID 904051Notes

Reaction equation

HRID 904051 reaction equation
[N+](=[CH2:3])=[N-].C(=O)(O)[O-].[Na+].[CH3:9][N:10]1[C:14]([OH:15])=[C:13]([C:16](=[O:27])[C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][C:18]=2[Cl:26])[C:12]([CH3:28])=[N:11]1>C(OCC)C.C(Cl)Cl.C1(C)C=CC=CC=1>[CH3:9][N:10]1[C:14]([O:15][CH3:3])=[C:13]([C:16](=[O:27])[C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][C:18]=2[Cl:26])[C:12]([CH3:28])=[N:11]1

Participants

7

Reactant 3

HCID 9550DiazomethaneHCID 516892Sodium BicarbonateHCID 178434076HCID 178434076, compound

Product 1

HCID 23333415HCID 23333415, compound

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent2×HCID 6344DichloromethaneSolvent

Procedure

In a four necked flask, 1.4 g of 1,3-dimethyl-4-(2-chloro-4-nitrobenzoyl)-5-hydroxypyrazole was dissolved in 10 ml of ethyl ether. The solution was cooled with ice-water and an ether solution of diazomethane was added and the reaction was carried out until ceasing nitrogen gas. Diazomethane and ether were distilled off from the reaction mixture to obtain the precipitate of the reaction product. The precipitate was dissolved in methylene chloride. The solution was mixed with a saturated aqueous solution of sodium bicarbonate. The organic phase was separated and methylene chloride was distilled off to obtain a solid product. The solid product was dissolved in toluene and adsorbed on a silica gel column and eluted with methylene chloride to obtain 0.8 g of 1,3-dimethyl-4-(2-chloro-4-nitrobenzoyl)-5-methoxy pyrazole having a melting point of 97° to 98° C.

Workup

  1. distillationDiazomethane and ether were distilled off from the reaction mixture
  2. customto obtain the precipitate of the reaction product
  3. customThe organic phase was separated
  4. distillationmethylene chloride was distilled off
  5. customto obtain a solid product
  6. washeluted with methylene chloride

Sources & evidence

ORD record
ord-cb267f9535d1418ba281282df877fe07
Source dataset
uspto-grants-1980_10
Patent number
US04230481

Reaction notes

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