Sodium Carbonate → HCID 67516544, compound

HRID 1754338Notes

Reaction equation

HRID 1754338 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH3:12])[C:5](=[NH:8])[NH:6][OH:7].Br[C:14]1C=C(C=CC=1C)C#N.Cl.NO.[C:26](=[O:29])([O-])[O-].[Na+].[Na+]>C(O)C.O>[Br:1][C:2]1[CH:3]=[C:4]([C:5]2[N:8]([CH3:14])[C:26](=[O:29])[O:7][N:6]=2)[CH:9]=[CH:10][C:11]=1[CH3:12]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 140048403-Bromo-4-methylbenzonitrileHCID 178425640HCID 178425640, compound

Product 1

HCID 67516544HCID 67516544, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Step-1: 3-Bromo-N-hydroxy-4-methylbenzimidamide: To a stirred solution of 3-bromo-4-methylbenzonitrile (2.0 g, 10.2 mmol, 1.0 eq) in ethanol (20 mL) was added hydroxylamine hydrochloride (1.77 g, 25.5 mmol, 2.5 eq) followed by a solution of sodium carbonate (2.70 g, 25.5 mmol, 2.5 eq) in water (2 mL). The resulting mixture was refluxed for 6 h. The reaction was cooled to room temperature and the solvent was removed under vacuum. The residue was taken in DCM (100 mL) and washed with water (30 mL), brine (30 mL), dried (Na2SO4) and filtered. The filtrate was rotary evaporated to afford 1.5 g of the title compound as a white solid. 1HNMR (400 MHz, CDCl3) δ 9.70 (s, 1H), 7.86 (d, J=1.5 Hz, 1H), 7.59 (dd, J=7.5, 1.5 Hz, 1H), 7.34 (d, J=8.0 Hz, 1H), 5.86 (s, 2H), 2.34 (s, 3H); ESI-MS (m/z) 229, 231 [(MH)+ Br79,81].

Workup

  1. temperatureThe resulting mixture was refluxed for 6 h
  2. customthe solvent was removed under vacuum
  3. washwashed with water (30 mL), brine (30 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customThe filtrate was rotary evaporated

Sources & evidence

ORD record
ord-ed38c03488d74fcfb2216655755b1305
Source dataset
uspto-grants-2015_10
Patent number
US09169242B2

Reaction notes

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