Phosphorus pentachloride → 2-chloro-6-fluoro-N-(4-iodophenyl)benzenecarbohydrazonoyl chloride

HRID 59228Notes

Reaction equation

HRID 59228 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[C:3]=1/[CH:4]=[N:5]/[NH:6][C:7]1[CH:12]=[CH:11][C:10]([I:13])=[CH:9][CH:8]=1.P(Cl)(Cl)(Cl)(Cl)[Cl:20]>C1C=CC=CC=1>[Cl:1][C:2]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[C:3]=1[C:4]([Cl:20])=[N:5][NH:6][C:7]1[CH:8]=[CH:9][C:10]([I:13])=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 90020166N-[(E)-(2-chloro-6-fluorophenyl)methylideneamino]-4-iodoaniline

Product 1

HCID 1317332342-chloro-6-fluoro-N-(4-iodophenyl)benzenecarbohydrazonoyl chlorideYield 76.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The title compound was prepared according to the procedure described in step-2 of Intermediate-1 using (1E)-1-(2-chloro-6-fluorobenzylidene)-2-(4-iodophenyl)hydrazine (1.2 g, 3.20 mmol), PCl5 (0.990 g, 4.8 mmol) and benzene (20 mL) to afford 1.0 g of desired product. 1H NMR. (300 MHz, DMSO d6): δ 7.00 (d, J=8.7 Hz, 2H), 7.41 (d, J=8.7 Hz, 1H), 7.48-7.60 (m, 4H), 10.22 (s, 1H).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-96078c6f0c624753b20010b26f0d8960
Source dataset
uspto-grants-2016_09
Patent number
US09439890B2

Reaction notes

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