Sodium Nitrite → HCID 58136805, compound

HRID 1258532Notes

Reaction equation

HRID 1258532 reaction equation
N[C:2]1[CH:3]=[C:4]([C:14](=[O:16])[CH3:15])[CH:5]=[C:6]([S:8]([F:13])([F:12])([F:11])([F:10])[F:9])[CH:7]=1.N([O-])=[O:18].[Na+]>S(=O)(=O)(O)O.O>[OH:18][C:2]1[CH:3]=[C:4]([C:14](=[O:16])[CH3:15])[CH:5]=[C:6]([S:8]([F:13])([F:12])([F:11])([F:10])[F:9])[CH:7]=1

Participants

5

Reactant 2

HCID 23668193Sodium NitriteHCID 581368521-[3-Amino-5-(pentafluorosulfanyl)phenyl]ethanone

Product 1

HCID 58136805HCID 58136805, compoundYield 54.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Conditions

Temperature
-5 °C

Procedure

1-[3-Amino-5-(pentafluorosulfanyl)phenyl]ethanone (3.00 g) was dissolved while heating in 35% aqueous sulfuric acid (25 ml). The solution was cooled to −5° C. and a solution of sodium nitrite (780 mg) in 15 ml of water was added dropwise within 10 min. After 40 min at −5° C., the cooling bath was removed and the mixture was heated to 100° C. for 2 h. After cooling, the mixture was extracted twice with EA. The combined EA phases were washed with saturated sodium hydrogencarbonate solution, dried, filtered and concentrated. The residue was purified using silica gel (80 g cartridge, n-heptane/MtB ether gradient of 0-100% within 40 min). 1.62 g of the title compound were obtained.

Workup

  1. customthe cooling bath was removed
  2. temperaturethe mixture was heated to 100° C. for 2 h
  3. temperatureAfter cooling
  4. extractionthe mixture was extracted twice with EA
  5. washThe combined EA phases were washed with saturated sodium hydrogencarbonate solution
  6. customdried
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified
  10. customsilica gel (80 g cartridge, n-heptane/MtB ether gradient of 0-100% within 40 min)

Sources & evidence

ORD record
ord-720e663eaed64bcf8ac71861e0931030
Source dataset
uspto-grants-2013_06
Patent number
US08466169B2

Reaction notes

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