Nitric Acid → HCID 71184081, compound

HRID 1422588Notes

Reaction equation

HRID 1422588 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]12[CH2:15][CH:14]1[CH2:13][CH2:12][S:11][C:10]([NH2:16])=[N:9]2.S(=O)(=O)(O)O.[N+:22]([O-])([OH:24])=[O:23].[OH-].[Na+]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:22]([O-:24])=[O:23])=[CH:4][C:3]=1[C:8]12[CH2:15][CH:14]1[CH2:13][CH2:12][S:11][C:10]([NH2:16])=[N:9]2

Participants

5

Reactant 4

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 71183892HCID 71183892, compound

Product 1

HCID 71184081HCID 71184081, compoundYield 68.6%

Conditions

Temperature
0 °C

Procedure

(1SR,7SR)-1-(2-Fluorophenyl)-4-thia-2-azabicyclo[5.1.0]oct-2-en-3-amine (intermediate A5a) (1.22 g, 5.16 mmol, Eq: 1.00) was dissolved in conc. sulfuric acid (20.3 g, 11.0 ml, 207 mmol, Eq: 40), then at 0° C. fuming nitric acid (488 mg, 321 μl, 7.74 mmol, Eq: 1.5) was added dropwise with an Eppendorf pipette. The light brown solution was stirred at 0° C. for 2 hours. The reaction mixture was poured on ice and basified with conc NaOH (pH=10) followed by the extraction with dichloromethane. The organic layer was separated, dried over Na2SO4, filtered and evaporated to dryness to give the (1SR,7SR)-1-(2-fluoro-5-nitrophenyl)-4-thia-2-azabicyclo[5.1.0]oct-2-en-3-amine (995 mg, 3.54 mmol, 68.5% yield). as a yellow solid. The crude product was used in the next step without further purification. MS (ISP): m/z=237.2 [(M+H)+].

Workup

  1. extractionfollowed by the extraction with dichloromethane
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-2784d14addce47c89b73867d6ec74943
Source dataset
uspto-grants-2015_01
Patent number
US08927535B2

Reaction notes

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