HCID 60207449, compound → HCID 60207450, compound

HRID 1192227Notes

Reaction equation

HRID 1192227 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:24])[C:7]=1[S:8][C:9]1[S:13][C:12]([C:14]([NH:16][CH2:17][CH2:18][CH2:19][OH:20])=[O:15])=[CH:11][C:10]=1[N+:21]([O-:23])=[O:22]>C(Cl)(Cl)Cl>[Cl:24][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([Cl:1])[C:7]=1[S:8][C:9]1[S:13][C:12]([C:14]([NH:16][CH2:17][CH2:18][CH:19]=[O:20])=[O:15])=[CH:11][C:10]=1[N+:21]([O-:23])=[O:22]

Participants

3

Reactant 1

HCID 60207449HCID 60207449, compound

Product 1

HCID 60207450HCID 60207450, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of 5-((3,5-dichloropyridin-4-yl)thio)-N-(3-hydroxypropyl)-4-nitrothiophene-2-carboxamide (800 mg, 1.2 mmol) in chloroform (15 mL) was added Dessmartin reagent (611 mg, 1.4 mmol) at 0° C. The resulting reaction mixture was warmed up to ambient temperature and stirred at this temperature for 6 hours. After this time, the reaction mixture was diluted with chloroform and washed with brine and water. The organic layer was separated, dried (Na2SO4) and concentrated. The crude residue was purified by silica gel chromatography using a 97:3 mixture of dichloromethane and methanol as eluent to afford the title product as a solid (430 mg, 89% yield). 1H NMR (400 MHz, d6-DMSO) δ: 9.64 (1H, s), 8.98 (2H, s), 8.91 (1H, m), 8.39 (1H, s), 3.46 (2H, m), 2.66 (2H, m). MS m/z: 404.04, 406.03 [M+H]+.

Workup

  1. customThe resulting reaction mixture
  2. washwashed with brine and water
  3. customThe organic layer was separated
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe crude residue was purified by silica gel chromatography
  7. additiona 97:3 mixture of dichloromethane and methanol as eluent

Sources & evidence

ORD record
ord-b72a563acd3247bea846e4b270460319
Source dataset
uspto-grants-2014_03
Patent number
US08680139B2

Reaction notes

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