Triethylamine → HCID 54084696, compound

HRID 328529Notes

Reaction equation

HRID 328529 reaction equation
Cl.[Br:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][NH2:10])=[CH:5][CH:4]=1.C(N(CC)CC)C.[Cl:18][C:19]1[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[CH:21][CH:20]=1>C(OCC)C>[Br:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]([C:23](=[O:24])[C:22]2[CH:26]=[CH:27][C:19]([Cl:18])=[CH:20][CH:21]=2)[NH2:10])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 85014-Chlorobenzoyl chlorideHCID 121574-Bromophenylhydrazine hydrochloride

Product 1

HCID 54084696HCID 54084696, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A mixture consisting of 44.7 g. (0.20 mole) p-bromophenylhydrazine hydrochloride, 250 ml. diethyl ether, 70 ml. (0.504 mole) triethylamine, and 35.0 g. (0.20 mole) p-chlorobenzoyl chloride in 50 ml. diethyl ether (mixed in that order at -5° to -15° C. during 20 minutes) was stirred continuously for about 16 hrs. at about 25° C. The reaction mixture was filtered, and the solids on the filter were washed with water and then recrystallized from 95% ethanol. There was thus obtained 15.5 g. p-chlorobenzoic acid (p-bromophenyl)hydrazide having a melting point of 185° C. (dec.). An analytical sample melting at 184.5° C. (dec.) was obtained after two recrystallizations from ethyl acetate.

Workup

  1. customat about 25° C
  2. filtrationThe reaction mixture was filtered
  3. washthe solids on the filter were washed with water
  4. customrecrystallized from 95% ethanol
  5. customAn analytical sample melting at 184.5° C. (dec.) was obtained
  6. customafter two recrystallizations from ethyl acetate

Sources & evidence

ORD record
ord-dccf8bc938c04badad8f18240be87be8
Source dataset
uspto-grants-1977_04
Patent number
US04017540

Reaction notes

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