Sodium Chloride → 2'-Ethoxy-2-nitrobiphenyl-4-yl amine

HRID 423862

Reaction equation

HRID 423862 reaction equation
O.[S-2].[Na+].[Na+].[S].[CH2:6]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][C:16]=1[N+:24]([O-:26])=[O:25])[CH3:7].[Na+].[Cl-]>O>[CH2:6]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][C:16]=1[N+:24]([O-:26])=[O:25])[CH3:7]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 5362487SulfurHCID 19906495Sodium sulfide monohydrateHCID 574826992'-Ethoxy-2,4-dinitro-biphenyl

Product 1

HCID 574827002'-Ethoxy-2-nitrobiphenyl-4-yl amineYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A clear orange-red solution of polysulfide (120 ml, 7.5 eq.), previously prepared by heating sodium sulfide monohydrate (10 g), sulfur (1.04 g) and water (160 ml), was added dropwise at 90° C. over 45 minutes to a suspension of 2′-ethoxy-2,4-dinitro-biphenyl (1.2 g, 4.0 mmol) in water (40 ml). The red-brown solution was heated at reflux for 1.5 h. The mixture was cooled to room temperature, and solid NaCl (5 g) was added. The solution was extracted with CH2Cl2 (3×50 mL), and the combined organic extracts was concentrated to provide 2′-ethoxy-2-nitrobiphenyl-4-yl amine (0.98 g, 95%) that was used in the next step without further purification. 1H NMR (300 MHz, CDCl3) δ 7.26 (m, 2H), 7.17 (d,J=2.7 Hz, 1H), 7.11 (d,J=7.8 Hz, 1H), 7.00 (t,J=6.9 Hz, 1H), 6.83 (m, 2H), 3.91 (q,J=6.9 Hz, 2H), 1.23 (t,J=7.2 Hz, 3H); HPLC ret. time 2.81 min, 10-100% CH3CN, 5 min gradient; ESI-MS 259.1 m/z (MH+).

Workup

  1. temperatureThe red-brown solution was heated
  2. temperatureat reflux for 1.5 h
  3. extractionThe solution was extracted with CH2Cl2 (3×50 mL)
  4. concentrationthe combined organic extracts was concentrated

Sources & evidence

ORD record
ord-fc07bb0b3d1f4fccb331fbd86b632956
Source dataset
uspto-grants-2012_01
Patent number
US08101767B2

Linked notes

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