Sodium methanethiolate → (4-Bromo-phenyl)-[4-(5-chloro-2-methyl-phenyl)-6-methylsulfanyl-[1,3,5]triazin-2-yl]-amine

HRID 1435741

Reaction equation

HRID 1435741 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:14]=[C:13](Cl)[N:12]=[C:11]([C:16]3[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=3[CH3:23])[N:10]=2)=[CH:4][CH:3]=1.[CH3:24][S-:25].[Na+]>O1CCCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:10]=[C:11]([C:16]3[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=3[CH3:23])[N:12]=[C:13]([S:25][CH3:24])[N:14]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 10179730(4-Bromo-phenyl)-[4-chloro-6-(5-chloro-2-methyl-phenyl)-[1,3,5]triazin-2-YL]-amine

Product 1

HCID 10112949(4-Bromo-phenyl)-[4-(5-chloro-2-methyl-phenyl)-6-methylsulfanyl-[1,3,5]triazin-2-yl]-amineYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of the title compound of Example 20 (234 mg, 0.57 mmol), sodium thiomethoxide (50 mg, 0.71 mmol), and tetrahydrofuran (5 ml) was stirred for 24 hours. After concentrating under reduced pressure, the residue was dissolved in dichloromethane (25 ml). The solution was washed with water (25 ml) and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with dichloromethane-hexane (1:1) to provide the title compound (137 mg, 57% yield). 1H NMR (DMSO-d6) 10.42 (s, 1H), 7.88 (s, 1H), 7.70 (s, 2H), 7.45-7.55 (m, 3H), 7.38 (m, 1H), 2.55 (s, 3H), 2.50 (s, 3H).

Workup

  1. concentrationAfter concentrating under reduced pressure
  2. dissolutionthe residue was dissolved in dichloromethane (25 ml)
  3. washThe solution was washed with water (25 ml)
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash chromatography on silica gel eluting with dichloromethane-hexane (1:1)

Sources & evidence

ORD record
ord-19055edf0b534c87881dd5fa256cadfe
Source dataset
uspto-grants-2009_11
Patent number
US07618968B2

Linked notes

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