Nitric Acid → HCID 59642132, compound

HRID 2080935Notes

Reaction equation

HRID 2080935 reaction equation
[F:1][S:2]([F:16])([F:15])([F:14])([F:13])[C:3]1[CH:4]=[C:5]([NH:9][C:10](=[O:12])[CH3:11])[CH:6]=[CH:7][CH:8]=1.[N+:17]([O-:20])([OH:19])=[O:18]>>[N+:17]([C:8]1[CH:7]=[CH:6][C:5]([NH:9][C:10](=[O:12])[CH3:11])=[CH:4][C:3]=1[S:2]([F:13])([F:14])([F:15])([F:16])[F:1])([O-:19])=[O:18].[N+:17]([C:6]1[CH:7]=[CH:8][C:3]([S:2]([F:16])([F:15])([F:1])([F:13])[F:14])=[CH:4][C:5]=1[NH:9][C:10](=[O:12])[CH3:11])([O-:20])=[O:18]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 12992036HCID 12992036, compound

Product 2

HCID 59642132HCID 59642132, compoundHCID 86599510HCID 86599510, compound

Conditions

Temperature
-40 °C

Procedure

20.00 g of N-(3-pentafluorosulfanylphenyl)acetamide (preparation as in Tetrahedron 56, (2000) 3399) were dissolved in portions at from −35° C. to −40° C. in 100 ml of 90% HNO3. The mixture was stirred at −40° C. for 15 minutes, then poured onto 1 kg of ice and stirred at RT for 1 h. The product was then filtered, washed with water and dried under reduced pressure. Chromatography on silica gel using DIP afforded 3.61 g of N-(4-nitro-3-pentafluorosulfanylphenyl)acetamide as well as 17.00 g of N-(2-nitro-5-pentafluorosulfanylphenyl)acetamide.

Workup

  1. stirringstirred at RT for 1 h
  2. filtrationThe product was then filtered
  3. washwashed with water
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-386449e0b2f64993aef8a6b0d277f7fd
Source dataset
uspto-grants-2011_04
Patent number
US07932416B2

Reaction notes

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