2-Chlorophenylhydrazine hydrochloride → HCID 23042016, compound

HRID 2166091Notes

Reaction equation

HRID 2166091 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1[C:4](Cl)=[O:5].Cl.[Cl:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[NH:20][NH2:21]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1[C:4]([NH:21][NH:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[Cl:13])=[O:5]

Participants

4

Reactant 2

HCID 4432872-Chlorophenylhydrazine hydrochlorideHCID 27365472-Chloro-6-fluorobenzoyl chloride

Product 1

HCID 23042016HCID 23042016, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

56.9 g (0.29 mol) of 2-chloro-6-fluorobenzoyl chloride are introduced dropwise into a solution, cooled to 0° C., of 52.8 g (0.29 mol) of 2-chlorophenylhydrazine hydrochloride in 290 ml of pyridine so that the temperature of the solution does not exceed 5° C. The solution is stirred at room temperature for 16 hours and the solvent is subsequently evaporated off azeotropically with toluene under reduced pressure. The resulting red-brown suspension is taken up in 350 ml of diethyl ether and the solution is washed in sequence twice with dilute hydrochloric acid and in each case once with 5% sodium bicarbonate solution and with saturated sodium chloride solution. The aqueous phases are back-extracted with 350 ml of diethyl ether and the combined organic phases are dried over anhydrous magnesium sulfate and then evaporated. After recrystallization of the residue from acetone/n-hexane there is obtained 2-chloro-6-fluoro-N'-(o-chlorophenyl)-benzhydrazide, m.p. 156°-158° C.; IR spectrum: 1692 cm-1.

Workup

  1. customdoes not exceed 5° C
  2. customthe solvent is subsequently evaporated off azeotropically with toluene under reduced pressure
  3. washthe solution is washed in sequence twice with dilute hydrochloric acid and in each case once with 5% sodium bicarbonate solution and with saturated sodium chloride solution
  4. extractionThe aqueous phases are back-extracted with 350 ml of diethyl ether
  5. dry with materialthe combined organic phases are dried over anhydrous magnesium sulfate
  6. customevaporated
  7. customAfter recrystallization of the residue from acetone/n-hexane there

Sources & evidence

ORD record
ord-8ddc0973a7d94f478145ce5436811a90
Source dataset
uspto-grants-1990_07
Patent number
US04943583

Reaction notes

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