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

HRID 2076131Notes

Reaction equation

HRID 2076131 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, 1.6 mmol) and anhydrous stannous chloride (1.52 g, 7.9 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 (100) [(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-5582cbe553334d499ebdac4009a965a1
Source dataset
uspto-grants-2011_04
Patent number
US07923450B2

Reaction notes

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