Triethylamine → N-(2,4-dichlorophenyl)ethanehydrazonoyl chloride

HRID 1612425Notes

Reaction equation

HRID 1612425 reaction equation
[ClH:1].[C:2](=[NH:7])(OCC)[CH3:3].C(N(CC)CC)C.[Cl:15][C:16]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=1[NH:23]N>C(Cl)Cl.Cl.C(=N)(OCC)C>[Cl:15][C:16]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=1[NH:23][N:7]=[C:2]([Cl:1])[CH3:3]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 408929(2,4-Dichlorophenyl)hydrazine2×HCID 2724290Ethanimidic acid, ethyl ester, hydrochloride (1:1)

Product 1

HCID 72815031N-(2,4-dichlorophenyl)ethanehydrazonoyl chlorideYield 93.4%

Reagents, catalysts & solvents 2

HCID 2724290Ethanimidic acid, ethyl ester, hydrochloride (1:1)CatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A stirred solution of 13.6 grams (0.1100 mole) of ethyl acetimidate hydrochloride and 13.2 grams (0.1300 mole) of triethylamine in 100 grams of methylene chloride was cooled to about 0° C. for five minutes, and 17.7 grams (0.1000 mole) of 2,4-dichlorophenylhydrazine (1) was added. Upon completion of addition the reaction mixture stirred at 0° C. for about one hour, then it was allowed to warm to ambient temperature where it stirred for about two hours. GC analysis of the reaction mixture indicated the presence of a small amount of unreacted (1). An additional 0.6 gram of ethyl acetimidate hydrochloride was added (total 14.2 gram—0.1150 mole), and the reaction mixture was stirred for an additional one hour. After this time the reaction mixture was washed with about 20 mL of water and dried with magnesium sulfate. The mixture was filtered, and the filtrate was concentrated under reduced pressure to a semi-solid residue. The residue was triturated with 20 mL of hexane, and the resultant solid was collected by filtration. The solid was washed with 50 mL of hexane and dried, yielding 20.4 grams (93.4% yield) of 2-(2,4-dichlorophenyl)hydrazidethaneimidic acid (A).

Workup

  1. additionUpon completion of addition the reaction mixture
  2. temperatureto warm to ambient temperature where it
  3. stirringstirred for about two hours
  4. stirringthe reaction mixture was stirred for an additional one hour
  5. washAfter this time the reaction mixture was washed with about 20 mL of water
  6. dry with materialdried with magnesium sulfate
  7. filtrationThe mixture was filtered
  8. concentrationthe filtrate was concentrated under reduced pressure to a semi-solid residue
  9. customThe residue was triturated with 20 mL of hexane
  10. filtrationthe resultant solid was collected by filtration
  11. washThe solid was washed with 50 mL of hexane
  12. customdried

Sources & evidence

ORD record
ord-201adbbde2794dbcbe2f6b4114297da0
Source dataset
uspto-grants-2006_01
Patent number
US06992221B2

Reaction notes

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