5-(2-Methoxy-4-nitro-phenyl)-2,4-dimethyl-thiazole → 4-(2,4-Dimethyl-thiazol-5-yl)-3-methoxy-phenylamine

HRID 1855507Notes

Reaction equation

HRID 1855507 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[CH:6]=[CH:5][C:4]=1[C:12]1[S:16][C:15]([CH3:17])=[N:14][C:13]=1[CH3:18]>C(O)C>[CH3:17][C:15]1[S:16][C:12]([C:4]2[CH:5]=[CH:6][C:7]([NH2:9])=[CH:8][C:3]=2[O:2][CH3:1])=[C:13]([CH3:18])[N:14]=1

Participants

3

Reactant 1

HCID 670961295-(2-Methoxy-4-nitro-phenyl)-2,4-dimethyl-thiazole

Product 1

HCID 670962794-(2,4-Dimethyl-thiazol-5-yl)-3-methoxy-phenylamineYield 75%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 5-(2-methoxy-4-nitro-phenyl)-2,4-dimethyl-thiazole (415 mg, 1.57 mmol) and anhydrous stannous chloride (1.52 g, 7.85 mmol) in ethanol (25 mL) was stirred at reflux for 3 hours. The yellow solution was evaporated and the residue dissolved in ethyl acetate. This solution was washed with 1N aqueous sodium hydroxide solution, twice with water, with brine, dried with magnesium sulfate and the solvent was evaporated to dryness. Column chromatography (50 g silica, heptane/ethyl acetate 30-60% v/v) afforded the title compound (276 mg, 75%) as a pale yellow solid. MS ISP (m/e): 235.2 [(M+H)+]. 1H NMR (CDCl3, 300 MHz): δ (ppm)=7.04 (d, 1H), 6.31 (m, 2H), 3.80 (s broad, 2H), 3.78 (s, 3H), 2.66 (s, 3H), 2.29 (s, 3H). Mp 112-115° C.

Workup

  1. temperatureat reflux for 3 hours
  2. customThe yellow solution was evaporated
  3. dissolutionthe residue dissolved in ethyl acetate
  4. washThis solution was washed with 1N aqueous sodium hydroxide solution, twice with water, with brine
  5. dry with materialdried with magnesium sulfate
  6. customthe solvent was evaporated to dryness

Sources & evidence

ORD record
ord-4d50734d32bc4adf810f27739d6bd6d3
Source dataset
uspto-grants-2015_02
Patent number
US08962834B2

Reaction notes

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