Sodium Nitrite → HCID 58136805, compound

HRID 657988Notes

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

Conditions

Temperature: -5 °C

Procedure

1-[3-Amino-5-(pentafluorosulfanyl)phenyl]ethanone (O4.050; 3.00 g) was dissolved in 35% aqueous sulfuric acid (25 ml) while heating. 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

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

Sources & evidence

ORD record: ord-a8345a17ba2740dabb86fb940532d074
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08076336B2

Reaction notes

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