2,4-Dichloro-1,3,5-triazine → 4-chloro-N-{3-[(methylsulfonyl)methyl]phenyl}-1,3,5-triazin-2-amine

HRID 855625Notes

Reaction equation

HRID 855625 reaction equation
[CH3:1][S:2]([CH2:5][C:6]1[CH:7]=[C:8]([CH:10]=[CH:11][CH:12]=1)[NH2:9])(=[O:4])=[O:3].C(N(C(C)C)CC)(C)C.[Cl:22][C:23]1[N:28]=[C:27](Cl)[N:26]=[CH:25][N:24]=1>C(#N)C>[Cl:22][C:23]1[N:28]=[CH:27][N:26]=[C:25]([NH:9][C:8]2[CH:10]=[CH:11][CH:12]=[C:6]([CH2:5][S:2]([CH3:1])(=[O:3])=[O:4])[CH:7]=2)[N:24]=1

Participants

5

Reactant 3

HCID 178102,4-Dichloro-1,3,5-triazineHCID 81531DiisopropylethylamineHCID 219563393-(Methanesulfonylmethyl)aniline

Product 1

HCID 219563434-chloro-N-{3-[(methylsulfonyl)methyl]phenyl}-1,3,5-triazin-2-amineYield 70.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a dry flask containing a magnetic stir bar and a nitrogen atmosphere was added 0.247 g (1.33 mmol) of 3-[(methylsulfonyl)methyl]aniline, 2 mL dry acetonitrile and 0.23 mL (1.3 mmol) of diisopropylethyl amine and resultant mixture cooled in an ice bath. To the cold solution was added a solution of 0.2 g (1.33 mmol) of 2,4-dichloro-1,3,5-triazine in 2.4 mL of dry acetonitrile over 1 min. The reaction mixture was stirred for ca. 16 hrs and 1 gram of silica gel was added. The mixture was concentrated in vacuo to dryness and applied to the top of column of silica gel and eluted with a 15-50% ethyl acetate/dichloromethane gradient. The proper fractions were combined and concentrated in vacuo to give 0.28 g (70%) of 4-chloro-N-{3-[(methylsulfonyl)methyl]phenyl}-1,3,5-triazin-2-amine as a white solid. HNMR: δ 10.83 (s, 1H), 8.64 (s, 1H), 7.63 (m, 2H), 7.4 (t, 1H), 7.25 (d, 1H), 4.48 (s, 2H), 2.94 (s, 3H); MS (ES+, m/z) 299, 301 (M+H).

Workup

  1. additionTo a dry flask containing a magnetic stir bar
  2. temperaturecooled in an ice bath
  3. addition1 gram of silica gel was added
  4. concentrationThe mixture was concentrated in vacuo to dryness
  5. washeluted with a 15-50% ethyl acetate/dichloromethane gradient
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-df85f531e822404aadb580060dfb8d28
Source dataset
uspto-grants-2007_08
Patent number
US07262203B2

Reaction notes

Loading…