Diphenyl Ether → HCID 20391367, compound

HRID 1863434Notes

Reaction equation

HRID 1863434 reaction equation
C[O:2][C:3](=O)[NH:4][N:5]=[CH:6][C:7]1[N:8]=[C:9]([C:13]2[CH:14]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:16]=[CH:17][CH:18]=2)[NH:10][C:11]=1[CH3:12].C1(OC2C=CC=CC=2)C=CC=CC=1>CCCCCC>[CH3:12][C:11]1[N:10]=[C:9]([C:13]2[CH:14]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:16]=[CH:17][CH:18]=2)[N:8]2[C:7]=1[CH:6]=[N:5][NH:4][C:3]2=[O:2]

Participants

4

Reactant 2

HCID 7583Diphenyl EtherHCID 136398813HCID 136398813, compound

Product 1

HCID 20391367HCID 20391367, compoundYield 155.2%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

3-{[5-Methyl-2-(α,α,α-trifluoro-m-tolyl)-4-imidazolyl]-methylene}carbazic acid methyl ester (3.0 g) is added rapidly to diphenyl ether (50 ml) preheated to 297° C., and the mixture is then kept at 297° for 15 minutes. The mixture is rapidly cooled to room temperature, hexane (50 ml) is added and the mixture filtered to yield 4.2 g yellow solid. This material is chromatographed on a silica gel column using a hexane-ethyl acetate mixture as eluent. The fractions found to be identical by TLC are combined to afford 1.86 g of the title product, m.p. 194°-194.5° C.

Workup

  1. custompreheated to 297° C.
  2. filtrationthe mixture filtered

Sources & evidence

ORD record
ord-547afc6932114ba690b447bb46eb5eda
Source dataset
uspto-grants-1979_09
Patent number
US04168964

Reaction notes

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