Nitric Acid → (R)-5-(2-fluoro-5-nitro-phenyl)-5-methyl-1,1-dioxo-1,2,5,6-tetrahydro-1lambda6-[1,4]thiazin-3-ylamine

HRID 920176Notes

Reaction equation

HRID 920176 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@:8]1([CH3:17])[CH2:13][S:12](=[O:15])(=[O:14])[CH2:11][C:10]([NH2:16])=[N:9]1.S(=O)(=O)(O)O.[N+:23]([O-])([OH:25])=[O:24].C([O-])(O)=O.[Na+]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:23]([O-:25])=[O:24])=[CH:4][C:3]=1[C@:8]1([CH3:17])[CH2:13][S:12](=[O:14])(=[O:15])[CH2:11][C:10]([NH2:16])=[N:9]1

Participants

5

Reactant 4

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 90067085(R)-5-(2-fluoro-phenyl)-5-methyl-1,1-dioxo-1,2,5,6-tetrahydro-1lambda6-[1,4]thiazin-3-ylamine

Product 1

HCID 118073003(R)-5-(2-fluoro-5-nitro-phenyl)-5-methyl-1,1-dioxo-1,2,5,6-tetrahydro-1lambda6-[1,4]thiazin-3-ylamineYield 100%

Procedure

To a solution of (R)-5-(2-fluoro-phenyl)-5-methyl-1,1-dioxo-1,2,5,6-tetrahydro-1λ6-[1,4]thiazin-3-ylamine (497 mg, 1.94 mmol, Eq: 1.00) in conc. sulfuric acid (14.8 g, 8.06 ml, 151 mmol, Eq: 78) was added at 0° C. 100% nitric acid (189 mg, 134 μl, 3.01 mmol, Eq: 1.55) and the mixture was stirred at 0° C. for 1 hour. Poured into sat NaHCO3-sol., extracted with ethyl acetate, the organic layer was dried over Na2SO4. Removal of the solvent in vacuum left the (R)-5-(2-fluoro-5-nitro-phenyl)-5-methyl-1,1-dioxo-1,2,5,6-tetrahydro-1λ6-[1,4]thiazin-3-ylamine (584 mg, 1.94 mmol, 100% yield) as a light yellow oil. MS (ISP): m/z=302.1 [M+H]+.

Workup

  1. additionPoured
  2. extraction, extracted with ethyl acetate
  3. dry with materialthe organic layer was dried over Na2SO4
  4. customRemoval of the solvent in vacuum

Sources & evidence

ORD record
ord-dd180434441a4810a7c4b276cb4490c0
Source dataset
uspto-grants-2016_03
Patent number
US09273042B2

Reaction notes

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