Cyanogen Bromide → HCID 20780031, compound

HRID 1295848Notes

Reaction equation

HRID 1295848 reaction equation
[N:1]#[C:2]Br.[F:4][C:5]1[CH:6]=[C:7]([NH2:21])[C:8]([NH:11][C:12]2[C:17]([CH3:18])=[CH:16][C:15]([CH3:19])=[CH:14][C:13]=2[CH3:20])=[CH:9][CH:10]=1>C(O)C>[F:4][C:5]1[CH:10]=[CH:9][C:8]2[N:11]([C:12]3[C:13]([CH3:20])=[CH:14][C:15]([CH3:19])=[CH:16][C:17]=3[CH3:18])[C:2]([NH2:1])=[N:21][C:7]=2[CH:6]=1

Participants

4

Reactant 2

HCID 10476Cyanogen BromideHCID 20780029HCID 20780029, compound

Product 1

HCID 20780031HCID 20780031, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of cyanogen bromide (2.67 g, 25.2 mmol) in anhydrous ethanol (10 mL) was added at 0° C. to a solution of 4-fluoro-N1-(2,4,6-trimethyl-phenyl)-benzene-1,2-diamine (4.74 g, 19.4 mmol) in anhydrous ethanol (20 mL) under nitrogen. The reaction mixture was warmed up to room temperature for 10 min, then was heated at 155° C. For 40 min with a flow of nitrogen to remove ethanol. Upon cooling to room temperature, the resulting solids were transferred to a separatory funnel via dichloromethane (70 mL), and washed sequentially with 1 N sodium hydroxide (2×35 mL), water and brine. The organic layer was dried over anhydrous sodium sulfate and solvents were removed in vacuo to afford the title compound as a red solid (5.11 g, 98% yield). The purity of this compound was determined to be 95% by LC/MS. 1H NMR (CDCl3, 300 MHz) δ 7.12 (dd, J=9.7, 2.4 Hz, 1H), 7.06 (s, 2H), 6.69 (td, J=9.1, 2.4 Hz, 1H), 6.56 (dd, J=8.5, 4.7 Hz, 1H), 2.38 (s, 3H), 1.98 (s, 6H); 13C NMR (CDCl3, 75 MHz) δ 161.0, 157.9, 154.2, 143.3, 139.9, 137.4, 129.8, 128.8, 107.8 (d, J=10.2 Hz), 106.9 (d, J=25.3 Hz), 103.1 (d, J=25.2 Hz)21.1, 17.5; Mass spec.: 270.17 (MH+).

Workup

  1. temperaturewas heated at 155° C
  2. customFor 40 min with a flow of nitrogen to remove ethanol
  3. temperatureUpon cooling to room temperature
  4. customthe resulting solids were transferred to a separatory funnel via dichloromethane (70 mL)
  5. washwashed sequentially with 1 N sodium hydroxide (2×35 mL), water and brine
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate and solvents
  7. customwere removed in vacuo

Sources & evidence

ORD record
ord-51fa81890bb8415fb43991968ef65c8d
Source dataset
uspto-grants-2007_07
Patent number
US07244746B2

Reaction notes

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