4-Bromobenzene-1,2-diamine → HCID 178506219, compound

HRID 1433195Notes

Reaction equation

HRID 1433195 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([NH2:9])[CH:3]=1.Cl.C(O[C:14](=N)[CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=1)C>CCO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[NH:8][C:14]([CH2:15][O:16][C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:24])([F:25])[F:26])=[CH:19][CH:18]=3)=[N:9][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 3235934-Bromobenzene-1,2-diamineHCID 690421402-(4-Trifluoromethyl-phenoxy)-acetimidic acid ethyl ester hydrochloride

Product 1

HCID 178506219HCID 178506219, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-bromo-phenylene-diamine (19.2 g, 0.103 mol) and 2-(4-trifluoromethyl-phenoxy)-acetimidic acid ethyl ester hydrochloride (35.0 g, 0.123 mol) in EtOH (377 mL) was stirred at room temperature for 12 hours. The reaction was concentrated to give a brown solid, which was partitioned between EtOAc and water. The organic fraction(s) were washed with brine, dried over Na2SO4, and the filtrate was concentrated to afford the title compound as a brown solid (100%). 1H NMR (400 MHz, CD3OD) δ (ppm): 7.74 (s, 1H), 7.62 (d, 2H, J=8.0 Hz), 7.50 (d, 1H, J=8.8 Hz), 7.39 (dd, 1H, J=8.4 Hz, J=1.6 Hz), 7.23 (d, 2H, J=8.4 Hz), 5.41 (s, 2H). Mass Spectrum (LCMS, ESI pos.) Calcd. For C15H11BrF3N2O: 372.2 (M+H), Found 372.9.

Workup

  1. concentrationThe reaction was concentrated
  2. customto give a brown solid, which
  3. customwas partitioned between EtOAc and water
  4. washThe organic fraction(s) were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-9fce070e86dd47df9b9d18a105b0b863
Source dataset
uspto-grants-2009_11
Patent number
US07612211B2

Reaction notes

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