HCID 59395064, compound → HCID 59395016, compound

HRID 383420Notes

Reaction equation

HRID 383420 reaction equation
[CH3:1][N:2]([CH3:19])[CH2:3][C:4]1[N:8]=[C:7]([C:9]2[CH:14]=[C:13]([CH3:15])[CH:12]=[CH:11][C:10]=2[N+:16]([O-])=O)[O:6][N:5]=1.S.[Na].[Na]>O1CCOCC1.O.ClCCl>[CH3:19][N:2]([CH2:3][C:4]1[N:8]=[C:7]([C:9]2[CH:14]=[C:13]([CH3:15])[CH:12]=[CH:11][C:10]=2[NH2:16])[O:6][N:5]=1)[CH3:1]

Participants

6

Reactant 2

HCID 59395064HCID 59395064, compoundHCID 86643093HCID 86643093, compound

Product 1

HCID 59395016HCID 59395016, compoundYield 86%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of N,N-dimethyl-1-[5-(5-methyl-2-nitro-phenyl)-1,2,4-oxadiazol-3-yl]methanamine (38 mg, 0.15 mmol) in dioxane (1 mL) at 80° C. was added a hot solution (80° C.) of disodium sulfur dihydride anion nonahydrate (70 mg, 0.29 mmol) in water (1 mL). The reaction was heated at 80° C. for 30 min then cooled to room temperature. The reaction was diluted with dichloromethane, washed with 50% saturated sodium bicarbonate solution (2×20 mL), and brine. The solution was dried over Na2SO4, filtered, and concentrated in vacuo to provide 2-(3-((dimethylamino)methyl)-1,2,4-oxadiazol-5-yl)-4-methylaniline (29 mg, 86% yield). LC/MS m/z 233.2 [M+H]+.

Workup

  1. temperaturethen cooled to room temperature
  2. washwashed with 50% saturated sodium bicarbonate solution (2×20 mL), and brine
  3. dry with materialThe solution was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a6769b706bf744e487cffd281e99bee4
Source dataset
uspto-grants-2013_02
Patent number
US08367660B2

Reaction notes

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