Nitric Acid → HCID 58493235, compound

HRID 1518928Notes

Reaction equation

HRID 1518928 reaction equation
[F:1][C:2]1[C:3]([CH3:18])=[C:4]([C:14]([OH:17])=[CH:15][CH:16]=1)[C:5]([O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:6].O.[N+:20]([O-])([OH:22])=[O:21]>C(Cl)Cl.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[F:1][C:2]1[C:3]([CH3:18])=[C:4]([C:14]([OH:17])=[C:15]([N+:20]([O-:22])=[O:21])[CH:16]=1)[C:5]([O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:6]

Participants

6

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 56950692HCID 56950692, compound

Product 1

HCID 58493235HCID 58493235, compoundYield 109.3%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
26 °C

Procedure

A 30 L 4-neck flask equipped with mechanical stirrer, thermometer and addition funnel was charged with a solution of compound 63 (1100 g, 4.47 mol) in CH2Cl2 (8.0 L) followed by water (8.1 L) and tetrabutyl ammonium bromide (144 g, 0.45 mol). Aqueous HNO3 (591 mL, 68 w %, 8.94 mol) was added to the stirred two-phase reaction mixture at 24˜27° C. over 3 min and the mixture was stirred at 24-28° C. for 20 h. The two layers were separated and the aqueous layer was extracted with CH2Cl2 (4×1.0 L). The organic layers were then combined and successively washed with water (3×1.0 L) and brine (2×2 L). The organic layer was dried over Na2SO4 and filtered and concentrated under reduce pressure to give 1423 g (>100%) of compound 64 as dark brown solid.

Workup

  1. customA 30 L 4-neck flask equipped with mechanical stirrer
  2. additionthermometer and addition funnel
  3. customThe two layers were separated
  4. extractionthe aqueous layer was extracted with CH2Cl2 (4×1.0 L)
  5. washsuccessively washed with water (3×1.0 L) and brine (2×2 L)
  6. dry with materialThe organic layer was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-bfd2ad2189b34c66ac81758a7f0a03c2
Source dataset
uspto-grants-2015_07
Patent number
US09073829B2

Reaction notes

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