Sodium Thiosulfate → HCID 90273223, compound

HRID 1050444Notes

Reaction equation

HRID 1050444 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH3:12])=[CH:5][C:6](=[O:11])[C:7]=1[N+:8]([O-:10])=[O:9].C1C(=O)N([I:20])C(=O)C1.[O-]S([O-])(=S)=O.[Na+].[Na+]>C(O)(=O)C>[I:20][C:5]1[C:6](=[O:11])[C:7]([N+:8]([O-:10])=[O:9])=[C:2]([CH3:1])[NH:3][C:4]=1[CH3:12]

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 120273N-IodosuccinimideHCID 5492052,6-Dimethyl-3-nitropyridin-4(1H)-one

Product 1

HCID 90273223HCID 90273223, compoundYield 69.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
105 °C

Procedure

To a suspension of 2,6-dimethyl-3-nitropyridin-4(1H)-one (0.44 g, 2.62 mmol) in acetic acid (13 mL) was added NIS (0.765 g, 3.40 mmol). The mixture was heated at 105° C. for 2 h, at which time it was poured into ice water (100 mL). The mixture was stirred for 15 min and cooled in a freezer for 15 min. To the cooled mixture was added 0.1M Na2S2O3 (1-2 mL) with swirling The solids were filtered, washed with water, air dried for 5 min, and further dried in a vacuum oven for 4 h to give 3-iodo-2,6-dimethyl-5-nitropyridin-4(1H)-one (596 mg, 1.824 mmol, 69.7% yield). 1H NMR (400 MHz, DMSO-d6) δ 2.28-2.31 (m, 3 H) 12.32 (br. s., 1 H). MS(ES) [M+H]+ 294.9.

Workup

  1. temperaturecooled in a freezer for 15 min
  2. filtrationwere filtered
  3. washwashed with water, air
  4. customdried for 5 min
  5. customfurther dried in a vacuum oven for 4 h

Sources & evidence

ORD record
ord-0298f4fd1a9546b0a8f667847d6702f3
Source dataset
uspto-grants-2016_07
Patent number
US09382234B2

Reaction notes

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