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

HRID 1405200Notes

Reaction equation

HRID 1405200 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.CCN(C(C)C)C(C)C.[Cl-].[CH3:19][CH:20]([S:22]([CH2:25][C:26]1[CH:27]=[C:28]([CH:30]=[CH:31][CH:32]=1)[NH3+:29])(=[O:24])=[O:23])[CH3:21]>C1COCC1.CC(O)C>[Cl:8][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH:29][C:28]2[CH:30]=[CH:31][CH:32]=[C:26]([CH2:25][S:22]([CH:20]([CH3:21])[CH3:19])(=[O:24])=[O:23])[CH:27]=2)[N:7]=1

Participants

5

Reactant 3

HCID 178102,4-Dichloro-1,3,5-triazineHCID 81531DiisopropylethylamineHCID 867296113-[(Propan-2-ylsulfonyl)methyl]anilinium chloride

Product 1

HCID 891559554-Chloro-N-{3-[(propan-2-ylsulfonyl)methyl]phenyl}-1,3,5-triazin-2-amineYield 268%

Reagents, catalysts & solvents 1

HCID 22597222Tetrahydrofuran 2-propanolSolvent2×

Procedure

To a stirred solution of 2,4-dichloro-1,3,5-triazine (150 mg, ABCR GmbH & CO. KG) in THF/i-PrOH (1:1; 1.9 mL) DIPEA (0.52 mL) was added at −40° C. Then a suspension of 3-[(propan-2-ylsulfonyl)methyl]anilinium chloride (250 mg) in THF/i-PrOH (1:1, 0.94 mL) was added at this temperature. Under stirring the temperature of the reaction mixture was slowly raised over 3 hours to 0° C. The reaction mixture was then concentrated in vacuo to give the crude title compound (876 mg) which was used without further purification.

Workup

  1. additionwas added at this temperature
  2. temperaturewas slowly raised over 3 hours to 0° C
  3. concentrationThe reaction mixture was then concentrated in vacuo

Sources & evidence

ORD record
ord-7869f1e9e48f40f3a59f40b90b39107a
Source dataset
uspto-grants-2014_12
Patent number
US08916557B2

Reaction notes

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