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

HRID 2304843Notes

Reaction equation

HRID 2304843 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([O:10][CH2:11][CH2:12][C:13]3[N:14]=[C:15]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[O:16][C:17]=3[CH3:18])[C:4]=2[CH:3]=[CH:2]1.[N+:25]([O-])([OH:27])=[O:26].C(=O)([O-])[O-].[Na+].[Na+]>C(O)(=O)C.O>[CH3:18][C:17]1[O:16][C:15]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[N:14][C:13]=1[CH2:12][CH2:11][O:10][C:9]1[C:4]2[CH:3]=[CH:2][S:1][C:5]=2[C:6]([N+:25]([O-:27])=[O:26])=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 944Nitric AcidHCID 10340Sodium CarbonateHCID 112329474-[2-(5-Methyl-2-phenyl-4-oxazolyl)ethoxy]benzothiophene

Product 1

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

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

286 g (0.853 mol) of 4-[2-(benzothiophene-4-yloxy)-ethyl]-5-methyl-2-phenyl-oxazole were suspended in 6.3 l of glacial acetic acid. Temperature was raised to 60 ° C. The resulting clear solution was cooled to 25° C. 132 ml (3.18 mol) of 100% nitric acid were added within 3 minutes. The reaction mixture was cooled below 30° C. After crystallization the suspension was stirred at 18 to 20° C. for 1 hour. The precipitate was filtered with suction and washed with 2×600 ml of tert-butyl methyl ether. The residue was suspended in 4 l of acetic ester for 15 minutes. 200 g (1.9 mol) of sodium carbonate in 3 l water were added. The resulting suspension was stirred for 1 hour. Acetic ester was distilled off followed by addition of 2 l of water. The suspension was stirred for 30 minutes. The precipitate was filtered with suction, washed with water and dried (50° C., 24 hours).

Workup

  1. temperatureThe resulting clear solution was cooled to 25° C
  2. temperatureThe reaction mixture was cooled below 30° C
  3. customAfter crystallization the suspension
  4. filtrationThe precipitate was filtered with suction
  5. washwashed with 2×600 ml of tert-butyl methyl ether
  6. waitThe residue was suspended in 4 l of acetic ester for 15 minutes
  7. stirringThe resulting suspension was stirred for 1 hour
  8. distillationAcetic ester was distilled off
  9. additionfollowed by addition of 2 l of water
  10. stirringThe suspension was stirred for 30 minutes
  11. filtrationThe precipitate was filtered with suction
  12. washwashed with water
  13. customdried (50° C., 24 hours)

Sources & evidence

ORD record
ord-120c12b18f484876b171e8472bafa1ae
Source dataset
uspto-grants-2002_08
Patent number
US06437144B1

Reaction notes

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