5-(2-Methoxy-4-nitro-phenyl)-2-methyl-thiazole → 3-Methoxy-4-(2-methyl-thiazol-5-yl)-phenylamine

HRID 2076127Notes

Reaction equation

HRID 2076127 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][CH:13]=1>C(O)C>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([NH2:9])[CH:6]=[CH:5][C:4]=1[C:12]1[S:16][C:15]([CH3:17])=[N:14][CH:13]=1

Participants

3

Reactant 1

HCID 670963525-(2-Methoxy-4-nitro-phenyl)-2-methyl-thiazole

Product 1

HCID 670959033-Methoxy-4-(2-methyl-thiazol-5-yl)-phenylamineYield 91.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 5-(2-methoxy-4-nitro-phenyl)-2-methyl-thiazole (330 mg, 1.32 mmol) and anhydrous stannous chloride (1.28 g, 6.59 mmol) in ethanol (21 mL) was stirred at reflux for 1 hour. The yellow solution is evaporated and the residue dissolved in ethyl acetate. This solution is washed twice with 2N aqueous sodium hydroxide solution, with brine, dried with magnesium sulfate and evaporated to dryness to afford the title compound (266 mg, 91%) as an orange solid. MS ISP (m/e): 221.2 (100) [(M+H)]. 1H NMR (CDCl3, 300 MHz): δ(ppm)=7.81 (s, 1H), 7.33 (d, 1H), 6.31 (m, 2H), 3.87 (s, 3H), 3.83 (m, 2H), 2.69 (s, 3H). mp 125-129° C.

Workup

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

Sources & evidence

ORD record
ord-d3de0e7fd8ab4530b258311813ed68ea
Source dataset
uspto-grants-2011_04
Patent number
US07923450B2

Reaction notes

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