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

HRID 1855504Notes

Reaction equation

HRID 1855504 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, 6.6 mmol) in ethanol (21 mL) was stirred at reflux for one hour. The yellow solution was evaporated and the residue dissolved in ethyl acetate. This solution was 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 [(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 one hour
  2. customThe yellow solution was evaporated
  3. dissolutionthe residue dissolved in ethyl acetate
  4. washThis solution was 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-594a650122d548a3b36daccf2611566b
Source dataset
uspto-grants-2015_02
Patent number
US08962834B2

Reaction notes

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