Ethanol → HCID 178506600, compound

HRID 2419791Notes

Reaction equation

HRID 2419791 reaction equation
[IH:1].[Cl:2][C:3]1[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[C:4]=1[CH:5]=[N:6][NH:7][C:8](=[NH:11])SC.[F:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22][NH2:23])=[CH:20][CH:19]=1.C(O)C>C(OCC)C>[IH:1].[Cl:2][C:3]1[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[C:4]=1[CH:5]=[N:6][NH:7][C:8]([NH:23][CH2:22][C:21]1[CH:24]=[CH:25][C:18]([F:17])=[CH:19][CH:20]=1)=[NH:11]

Participants

5

Reactant 3

HCID 702Ethanol2×HCID 673264-FluorobenzylamineHCID 178504060Methyl 3-(2,6-dichlorobenzylidene)thiocarbazimidate hydroiodide

Product 1

HCID 178506600HCID 178506600, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 5.85 g. of methyl 3-(2,6-dichlorobenzylidene)thiocarbazimidate hydroiodide (U.S. Pat. No. 3,657,337) and 3.75 g. of p-fluorobenzylamine in 25 ml. of absolute ethanol is heated under reflux for 24 hours and then evaporated under reduced pressure, giving a mixture of gum and crystals. This mixture is dissolved in 50 ml. of absolute ethanol and diluted with 175 ml. of diethyl ether. The colorless plates which form are removed by filtration and discarded. The filtrate is diluted with petroleum ether (b.p. 30°-60° C), causing colorless needles to separate. These needles are removed by filtration and recrystallized from a mixture of ethanol-diethyl ether-petroleum ether (b.p. 30°-60° C), giving the desired product as colorless crystals, m.p. 162.5°-164° C.

Workup

  1. temperatureunder reflux for 24 hours
  2. customevaporated under reduced pressure
  3. customgiving
  4. additiona mixture of gum and crystals
  5. dissolutionThis mixture is dissolved in 50 ml
  6. customThe colorless plates which form are removed by filtration
  7. additionThe filtrate is diluted with petroleum ether (b.p. 30°-60° C)
  8. customto separate
  9. customThese needles are removed by filtration
  10. customrecrystallized from a mixture of ethanol-diethyl ether-petroleum ether (b.p. 30°-60° C)

Sources & evidence

ORD record
ord-c453b6f518ae4a0fbf3e67178a8ebdfb
Source dataset
uspto-grants-1978_08
Patent number
US04107326

Reaction notes

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