Nitric Acid → HCID 11816733, compound

HRID 1368017Notes

Reaction equation

HRID 1368017 reaction equation
[Cl:1][C:2]1[C:10]2[O:9][C:8]([CH2:11][CH3:12])=[N:7][C:6]=2[C:5]([N+:13]([O-])=O)=[C:4]([F:16])[CH:3]=1.[Cl:17][C:18]1[C:26]2[O:25][C:24]([CH2:27][CH3:28])=[N:23][C:22]=2[CH:21]=[C:20]([F:29])[CH:19]=1.S(=O)(=O)(O)O.[N+:35]([O-])([OH:37])=[O:36]>>[NH2:13][C:5]1[C:6]2[N:7]=[C:8]([CH2:11][CH3:12])[O:9][C:10]=2[C:2]([Cl:1])=[CH:3][C:4]=1[F:16].[Cl:17][C:18]1[C:26]2[O:25][C:24]([CH2:27][CH3:28])=[N:23][C:22]=2[CH:21]=[C:20]([F:29])[C:19]=1[N+:35]([O-:37])=[O:36]

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 11435574HCID 11435574, compoundHCID 12056910HCID 12056910, compound

Product 2

HCID 11816733HCID 11816733, compoundHCID 18519627HCID 18519627, compound

Procedure

Step 4 Preparation of 7-Chloro-2-ethyl-5-fluoro-4-nitrobenzoxazole as an Intermediate 7-Chloro-2-ethyl-5-fluorobenzoxazole (0.9 g) was slowly added to a mixture of sulfuric acid (9 ml) and nitric acid (0.6 ml) at −40° C. The dryice-acetone bath was removed and the mixture stirred for 2 hours. Ice-water was added and the mixture was extracted with ether. The organic phase was dried over anhydrous sodium sulfate and concentrated to an oil under reduced pressure. The residue was purified by column chromatography on silica gel using 5% ether in hexane. The desired product was obtained as a white solid [0.35 g, 1H-NMR (CDCl3, 300 MHz): 1.48(3H, t, J=7.6 Hz), 3.07(2H, q, J=7.6 Hz), 7.27(1H, d, J=10.5 Hz) ppm], along with a by-product, 7-chloro-2-ethyl-5-fluoro-6-nitrobenzoxazole (0.49 g).

Workup

  1. customThe dryice-acetone bath was removed
  2. additionIce-water was added
  3. extractionthe mixture was extracted with ether
  4. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  5. concentrationconcentrated to an oil under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel using 5% ether in hexane

Sources & evidence

ORD record
ord-cb5ae0fd0ee0466ba48fe96ce6b175be
Source dataset
uspto-grants-2003_06
Patent number
US06573218B1

Reaction notes

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