HCID 59395064, compound → HCID 59395016, compound

HRID 1465140Notes

Reaction equation

HRID 1465140 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.O.O.O.O.O.O.O.O.O.[S-][S-].[Na+].[Na+]>O1CCOCC1.O>[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

5

Reactant 2

HCID 59395064HCID 59395064, compoundHCID 145850454HCID 145850454, compound

Product 1

HCID 59395016HCID 59395016, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of N,N-dimethyl-1-(5-(5-methyl-2-nitrophenyl)-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 sodium disulfide nonahydrate (70 mg, 0.29 mmol) in water (1 mL). The reaction was heated at 80° C. for 30 min resulting in clean conversion to the desired product. The reaction was diluted with dichloromethane then washed with 50% saturated NaHCO3 (2×20 mL) and brine. The solution was dried over Na2SO4, filtered and dried down to provide 2-(3-((dimethylamino)methyl)-1,2,4-oxadiazol-5-yl)-4-methylaniline as a light orange oil (29 mg, 86% yield). LC/MS m/z 233.2 [M+H]+.

Sources & evidence

ORD record
ord-6dc082980bbb4a40bf37bb56c521fb46
Source dataset
uspto-grants-2015_04
Patent number
US08999976B2

Reaction notes

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