Chlorobenzene → HCID 69905525, compound

HRID 2203199Notes

Reaction equation

HRID 2203199 reaction equation
[NH2:1][C:2](=[O:15])/[C:3](/[C:13]#[N:14])=[N:4]/[NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[Br:12].[Al+3].[Cl-].[Cl-].[Cl-].[Cl:20]C1C=CC=CC=1>Cl>[ClH:20].[NH2:14][C:13]1[C:11]2[C:6](=[C:7]([Br:12])[CH:8]=[CH:9][CH:10]=2)[N:5]=[N:4][C:3]=1[C:2]([NH2:1])=[O:15]

Participants

6

Reactant 3

HCID 7964ChlorobenzeneHCID 6451240Aluminum(III) ChlorideHCID 88045548HCID 88045548, compound

Product 2

HCID 313Hydrochloric AcidHCID 69905525HCID 69905525, compoundYield 62.5%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

(E)-2-Amino-N′-(2-bromophenyl)-2-oxoacetohydrazonoyl cyanide (50.1 g, 187.5 mmol), AlCl3 (100 g, 750 mmol), and chlorobenzene (419 mL, 412 mol) were stirred at 115° C. overnight under N2. The reaction mixture was subsequently cooled to RT and 2M HCl (820 mL) was slowly added. The reaction mixture was stirred at 100° C. for 1 hour and then cooled. The product was collected by vacuum filtration, rinsed with EtOH (200 mL) and Et2O (100 mL), and dried under high vacuum to give an HCl salt of the title compound as a yellow solid (31.25 g, 62.5%). 1H NMR (400 MHz, DMSO-d6) δ ppm 9.91 (1H, s), 9.43 (1H, s), 8.61-8.59 (1H, d, J=8.4 Hz), 8.43 (1H, s), 8.32-8.30 (1H, d, J=7.6 Hz), 7.94 (1H, s), 7.69-7.65 (1H, m); LC-MS (5-95% ACN in H2O gradient with 0.02% NH4OAc, tR 2.659 minutes) ESI+APCI m/z [M+H]+ 267.

Workup

  1. temperaturecooled
  2. filtrationThe product was collected by vacuum filtration
  3. washrinsed with EtOH (200 mL) and Et2O (100 mL)
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-cacd18c0a1a042c0ab74adb9f36aa78e
Source dataset
uspto-grants-2016_06
Patent number
US09365566B2

Reaction notes

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