Hydrochloric Acid → HCID 89825661, compound

HRID 2203201Notes

Reaction equation

HRID 2203201 reaction equation
[NH2:1][C:2](=[O:16])/[C:3](/[C:14]#[N:15])=[N:4]/[NH:5][C:6]1[CH:11]=[C:10]([F:12])[CH:9]=[CH:8][C:7]=1[Br:13].[Al+3].[Cl-].[Cl-].[Cl-].C1(C)C=CC=CC=1.Cl>CCO>[NH2:15][C:14]1[C:11]2[C:6](=[C:7]([Br:13])[CH:8]=[CH:9][C:10]=2[F:12])[N:5]=[N:4][C:3]=1[C:2]([NH2:1])=[O:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 6451240Aluminum(III) ChlorideHCID 89825272HCID 89825272, compound

Product 1

HCID 89825661HCID 89825661, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

(E)-2-Amino-N′-(2-bromo-5-fluorophenyl)-2-oxoacetohydrazonoyl cyanide (10 g, 35 mmol), AlCl3 (20 g, 4.0 eq), and toluene (200 mL) were stirred at 120° C. overnight under N2. The reaction mixture was subsequently cooled to 0° C. and 2N HCl (200 mL) was added. The reaction mixture was stirred at 0° C. for 10 minutes and then filtered to afford a crude solid (4.5 g), which was dispersed in EtOH (500 mL). The mixture was stirred at RT for 4 hours and filtered. The filtrate was concentrated to give the title compound (1.5 g, 15%). 1H NMR (400 MHz, DMSO-d6) δ ppm 9.72 (1H, s), 8.62 (1H, s), 8.23-8.20 (1H, m), 8.00 (1H, s), 7.80 (1H, s), 7.47-7.42 (1H, m); LC-MS (5-95% ACN in H2O gradient with 0.02% NH4OAc, tR 3.020 minutes) ESI+APCI m/z [M+H]+ 285.

Workup

  1. filtrationfiltered
  2. customto afford a crude solid (4.5 g), which
  3. stirringThe mixture was stirred at RT for 4 hours
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-e1d33af73cb647548f8691daab20eff6
Source dataset
uspto-grants-2016_06
Patent number
US09365566B2

Reaction notes

Loading…