5-Methyl-4-[2-(7-nitro-benzothiophene-4-yloxy)-ethyl]-2-phenyl-oxazole → 5-Methyl-4-[2-(7-amino-benzothiophene-4-yloxy)-ethyl]-2-phenyl-oxazole

HRID 2304844Notes

Reaction equation

HRID 2304844 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][O:15][C:16]1[C:21]2[CH:22]=[CH:23][S:24][C:20]=2[C:19]([N+:25]([O-])=O)=[CH:18][CH:17]=1>C1COCC1>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][O:15][C:16]1[C:21]2[CH:22]=[CH:23][S:24][C:20]=2[C:19]([NH2:25])=[CH:18][CH:17]=1

Participants

3

Reactant 1

HCID 154856645-Methyl-4-[2-(7-nitro-benzothiophene-4-yloxy)-ethyl]-2-phenyl-oxazole

Product 1

HCID 154856655-Methyl-4-[2-(7-amino-benzothiophene-4-yloxy)-ethyl]-2-phenyl-oxazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

50 g (1.052 mol) of 5-methyl-4-[2-(7-nitro-benzothiophene-4-yloxy)-ethyl]-2-phenyl-oxazole were solved in 1 l of THF at 20 to 25 ° C. 75 ml Lewatit M 600 (OH31-form) (Bayer AG) were washed with about 100 ml THF, added to the 5-methyl-4-[2-(7-nitro-benzothiophene-4-yloxy)-ethyl]-2-phenyl-oxazole solution and stirred at room temperature for 1 hour. Then the Lewatit M 600 material was filtered with suction and washed with 100 ml THF. 12.5 g of Raney nickel were added to the combined THF solutions followed by hydrogenation of the 5-methyl-4-[2-(7-nitro-benzothiophene-4-yloxy)-ethyl]-2-phenyl-oxazole at standard pressure. The temperature of the reaction mixture should not exceed 35 to 40° C. Hydrogen pressure was increased to 6 bar within 6 hours. After hydrogenation the reaction mixture was stirred for 1 hour. Then the catalyst was filtered with suction, the THF was distilled off, 180 ml ethanol was added and the residue was boiled out for 30 minutes. The reaction mixture was stirred at 0° C. for 1 hour. The precipitate was filtered with suction and the residue was washed with 25 ml ethanol and dried for 24 hours at 50° C. (vacuum).

Workup

  1. wash75 ml Lewatit M 600 (OH31-form) (Bayer AG) were washed with about 100 ml THF
  2. additionadded to the 5-methyl-4-[2-(7-nitro-benzothiophene-4-yloxy)-ethyl]-2-phenyl-oxazole solution
  3. filtrationThen the Lewatit M 600 material was filtered with suction
  4. washwashed with 100 ml THF
  5. addition12.5 g of Raney nickel were added to the combined THF solutions
  6. customexceed 35 to 40° C
  7. temperatureHydrogen pressure was increased to 6 bar within 6 hours
  8. stirringAfter hydrogenation the reaction mixture was stirred for 1 hour
  9. filtrationThen the catalyst was filtered with suction
  10. distillationthe THF was distilled off
  11. addition180 ml ethanol was added
  12. waitthe residue was boiled out for 30 minutes
  13. stirringThe reaction mixture was stirred at 0° C. for 1 hour
  14. filtrationThe precipitate was filtered with suction
  15. washthe residue was washed with 25 ml ethanol
  16. customdried for 24 hours at 50° C. (vacuum)

Sources & evidence

ORD record
ord-09af7de434644c27a15ed99c950c6f09
Source dataset
uspto-grants-2002_08
Patent number
US06437144B1

Reaction notes

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