Triethylamine → 3,6-dichloro-N-[2-(propan-2-ylsulfonyl)phenyl]-1,2,4-triazin-5-amine

HRID 921441Notes

Reaction equation

HRID 921441 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([CH:11]([CH3:13])[CH3:12])(=[O:10])=[O:9].[Cl:14][C:15]1[N:16]=[N:17][C:18]([Cl:22])=[C:19](Cl)[N:20]=1.C(N(CC)CC)C>C(Cl)Cl>[Cl:14][C:15]1[N:16]=[N:17][C:18]([Cl:22])=[C:19]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[S:8]([CH:11]([CH3:13])[CH3:12])(=[O:10])=[O:9])[N:20]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 122624033,5,6-Trichloro-1,2,4-triazineHCID 126463662-(Propane-2-sulfonyl)aniline

Product 1

HCID 866688223,6-dichloro-N-[2-(propan-2-ylsulfonyl)phenyl]-1,2,4-triazin-5-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-Amino-2-(isopropylsulphonyl)benzene (350 mg, 1.6 mmol) and 3,5,6-trichloro-1,2,4-triazine (1.6 mmol) in CH2Cl2, is added triethylamine (2 mmol). The reaction mixture is allowed to cool to room temperature, dissolved in dichloromethane and washed with an aqueous solution of Na2CO3. The dichloromethane extract is dried over MgSO4 and evaporated. The crude product is purified by Prep-HPLC.

Workup

  1. washwashed with an aqueous solution of Na2CO3
  2. extractionThe dichloromethane extract
  3. dry with materialis dried over MgSO4
  4. customevaporated
  5. customThe crude product is purified by Prep-HPLC

Sources & evidence

ORD record
ord-fb6effa6462c4cf79514f454cc74f13e
Source dataset
uspto-grants-2016_03
Patent number
US09273077B2

Reaction notes

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