Triethylamine → {5-[4-Amino-6-(2-methoxy-phenylsulfanyl)-[1,3,5]triazin-2-yl]-2,4-dichlorophenoxy}-acetonitrile

HRID 217282

Reaction equation

HRID 217282 reaction equation
C(N(CC)CC)C.[CH3:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[SH:16].[NH2:17][C:18]1[N:23]=[C:22](S(CC2C=CC=CC=2)=O)[N:21]=[C:20]([C:33]2[C:34]([Cl:44])=[CH:35][C:36]([Cl:43])=[C:37]([CH:42]=2)[O:38][CH2:39][C:40]#[N:41])[N:19]=1>CN(C)C=O>[NH2:17][C:18]1[N:23]=[C:22]([S:16][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[O:9][CH3:8])[N:21]=[C:20]([C:33]2[C:34]([Cl:44])=[CH:35][C:36]([Cl:43])=[C:37]([CH:42]=2)[O:38][CH2:39][C:40]#[N:41])[N:19]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 23642ThioguaiacolHCID 57898869[5-(4-Amino-6-phenylmethanesulfinyl-[1,3,5]triazin-2-yl)-2,4-dichlorophenoxy]-acetonitrile

Product 1

HCID 57898818{5-[4-Amino-6-(2-methoxy-phenylsulfanyl)-[1,3,5]triazin-2-yl]-2,4-dichlorophenoxy}-acetonitrileYield 83.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Triethylamine (12 μL) and 2-methoxybenzenethiol (12 mg) were added in succession to a solution of the above-described [5-(4-amino-6-phenylmethanesulfinyl-[1,3,5]triazin-2-yl)-2,4-dichlorophenoxy]-acetonitrile (12 mg) in dimethylformamide (0.5 mL). The mixture was stirred at room temperature for 8 hours. After dilution with ethyl acetate (7 mL), the mixture was washed twice with water and once with brine. The mixture was pre-dried over anhydrous sodium sulfate, and filtered. The solvent was distilled off. The resulting residue was purified by silica gel column chromatography (developing solvent: hexane:ethyl acetate=7:3) to give {5-[4-amino-6-(2-methoxy-phenylsulfanyl)-[1,3,5]triazin-2-yl]-2,4-dichlorophenoxy}-acetonitrile as white solid (10 mg).

Workup

  1. washAfter dilution with ethyl acetate (7 mL), the mixture was washed twice with water and once with brine
  2. dry with materialThe mixture was pre-dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. distillationThe solvent was distilled off
  5. customThe resulting residue was purified by silica gel column chromatography (developing solvent: hexane:ethyl acetate=7:3)

Sources & evidence

ORD record
ord-ef965fb2a051411791d949e5a75fcaf6
Source dataset
uspto-grants-2012_06
Patent number
US08193351B2

Linked notes

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