Sodium Sulfide → HCID 58075503, compound

HRID 475724Notes

Reaction equation

HRID 475724 reaction equation
O1CCOCC1.[Cl:7][C:8]1[N:12]=[CH:11][N:10]([C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][C:14]=2[O:22][CH3:23])[N:9]=1.[S-2].[Na+].[Na+]>O>[Cl:7][C:8]1[N:12]=[CH:11][N:10]([C:13]2[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][C:14]=2[O:22][CH3:23])[N:9]=1

Participants

5

Reactant 3

HCID 14804Sodium SulfideHCID 312751,4-DioxaneHCID 580757403-chloro-1-(2-methoxy-4-nitrophenyl)-1H-1,2,4-triazole

Product 1

HCID 58075503HCID 58075503, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
75 °C

Procedure

Water (8 mL) and dioxane (8 mL) were added to a mixture of 3-chloro-1-(2-methoxy-4-nitrophenyl)-1H-1,2,4-triazole (0.900 g, 3.53 mmol) and sodium sulfide (1.379 g, 17.67 mmol) in a 20 mL vial. The vial was capped and heated at 70-80° C. for 24 hours. The mixture was cooled to rt, poured into water (300 mL) and extracted with EtOAc (2×150 mL). The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo to afford 4-(3-chloro-1H-1,2,4-triazol-1-yl)-3-methoxyaniline (577 mg, 73%) as a brown solid. LC-MS (M+H)+ 225.1.

Workup

  1. customThe vial was capped
  2. temperatureThe mixture was cooled to rt
  3. extractionextracted with EtOAc (2×150 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-92113131d2ac4a0e94b8b440a50f665b
Source dataset
uspto-grants-2014_01
Patent number
US08637525B2

Reaction notes

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