Sodium ethanethiolate → 5-(Ethylthio)-3-(2-methyl-3-nitrophenyl)-1,2,4-triazin-6-amine

HRID 445923Notes

Reaction equation

HRID 445923 reaction equation
Cl[C:2]1[N:3]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[C:10]=2[CH3:18])[N:5]=[N:6][C:7]=1[NH2:8].[CH2:19]([S-:21])[CH3:20].[Na+].CO.C(Cl)Cl>CN(C=O)C.C(OCC)(=O)C>[CH2:19]([S:21][C:2]1[N:3]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[C:10]=2[CH3:18])[N:5]=[N:6][C:7]=1[NH2:8])[CH3:20]

Participants

6

Reactant 3

HCID 4459711Sodium ethanethiolateHCID 21226129Dichloromethane methanolHCID 582795485-Chloro-3-(2-methyl-3-nitrophenyl)-1,2,4-triazin-6-amine

Product 1

HCID 582795465-(Ethylthio)-3-(2-methyl-3-nitrophenyl)-1,2,4-triazin-6-amineYield 91%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-chloro-3-(2-methyl-3-nitrophenyl)-1,2,4-triazin-6-amine (Ex. 1, A) (1.34 g, 5.04 mmol) in DMF (30 mL) at 0° C. was added sodium ethanethiolate (0.509 g, 6.05 mmol) in one portion. The resulting mixture was stirred at rt for 1 hr before it was diluted with ethyl acetate (300 mL) and washed sequentially with 5% NaHCO3 (50 mL), water (2×50 mL), and brine (50 mL). The organic layer was dried over anhydrous MgSO4 and concentrated under vacuum. The product, 5-(ethylthio)-3-(2-methyl-3-nitrophenyl)-1,2,4-triazin-6-amine (1.333 g, 4.58 mmol, 91% yield), was isolated as a yellow solid by ISCO (120 g silica gel, solid loading, 2-5% MeOH/CH2Cl2).

Workup

  1. washwashed sequentially with 5% NaHCO3 (50 mL), water (2×50 mL), and brine (50 mL)
  2. dry with materialThe organic layer was dried over anhydrous MgSO4
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-d9cac1cf21d240748316b6ac84e53537
Source dataset
uspto-grants-2013_07
Patent number
US08476430B2

Reaction notes

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