Glycol monoethyl ether → HCID 13127588, compound

HRID 1462138Notes

Reaction equation

HRID 1462138 reaction equation
[C:1]([C:3]1[CH:4]=[N:5][N:6]([C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[C:29]([Cl:34])[C:28]=2[Cl:35])[C:7]=1[N:8]([C:18]([O:20][C:21]1C=CC=C[CH:22]=1)=[O:19])C(OC1C=CC=CC=1)=O)#[N:2].[CH2:36]([O:38]CCO)[CH3:37]>>[C:1]([C:3]1[CH:4]=[N:5][N:6]([C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[C:29]([Cl:34])[C:28]=2[Cl:35])[C:7]=1[NH:8][C:18]([O:20][CH2:21][CH2:22][O:38][CH2:36][CH3:37])=[O:19])#[N:2]

Participants

3

Reactant 2

HCID 8076Glycol monoethyl etherHCID 13127534HCID 13127534, compound

Product 1

HCID 13127588HCID 13127588, compound

Procedure

A stirred mixture of 4-cyano-5-di(phenoxycarbonyl)amino-1-(2,3,4-trichlorophenyl)pyrazole (prepared as described in Example 27; 20 g) in 2-ethoxyethanol (400 ml) was heated at reflux for 4 hours. The reaction mixture was evaporated to dryness and the residue crystallized from ethyl acetate-n-hexane to give 4-cyano-5-[(2-ethoxy)ethoxycarbonylamino]-1-(2,3,4-trichlorophenyl)pyrazole (10 g), m.p. 122°-124° C., in the form of colourless crystals. The mother liquors were evaporated to dryness and the residue chromatographed on aluminium oxide (120 g; May & Baker grade) using dichloromethane as eluent. Evaporation of the eluate and crystallisation of the residue from ethyl acetate-n-hexane gave a further quantity of 4-cyano-[5-(2-ethoxy)ethoxycarbonylamino]-1-(2,3,4-trichlorophenyl)pyrazole (3 g).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 hours
  3. customThe reaction mixture was evaporated to dryness
  4. customthe residue crystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-3e1627085cea4005b2717b295d89a541
Source dataset
uspto-grants-1984_07
Patent number
US04459150

Reaction notes

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