Cyanuric chloride → HCID 12148695, compound

HRID 1007191Notes

Reaction equation

HRID 1007191 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.N1C(Cl)=NC(Cl)=NC=1Cl.[CH3:21][O:22][C:23]1[CH:29]=[CH:28][C:26]([NH2:27])=[C:25]([N+:30]([O-:32])=[O:31])[CH:24]=1.C(N(CC)CC)C>C(Cl)Cl.C(OCC)(=O)C>[Cl:1][C:2]1[C:3]([C:4]([NH:27][C:26]2[CH:28]=[CH:29][C:23]([O:22][CH3:21])=[CH:24][C:25]=2[N+:30]([O-:32])=[O:31])=[O:6])=[CH:7][CH:8]=[C:9]([Cl:11])[N:10]=1

Participants

7

Reactant 4

HCID 7954Cyanuric chlorideHCID 8471TriethylamineHCID 667934-Methoxy-2-nitroanilineHCID 8540472,6-Dichloronicotinic acid

Product 1

HCID 12148695HCID 12148695, compoundYield 22.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2,6-dichloronicotinic acid (100 mg, 0.52 mmol) in CH2Cl2 (10 mL) was added cyanuric chloride (96 mg, 0.52 mmol). The mixture was stirred for half an hour, then 4-methoxy-2-nitroaniline (88 mg, 0.52 mmol) and triethylamine (0.1 mL, 0.72 mmol) were added. The resulting mixture was stirred at room temperature overnight and then diluted with ethyl acetate, washed with water. The organic phase was separated, dried over anhydrous Na2SO4, concentrated and purified by chromatography to give the title compound (40 mg, 22%) as a yellow solid. 1H NMR (DMSO-d6): 10.84 (bs, 1H), 8.09 (d, J=7.8, 1H), 7.75 (d, J=7.8, 1H), 7.57-7.52 (m, 2H), 7.37-7.33 (m, 1H), 3.86 (s, 3H).

Workup

  1. stirringThe resulting mixture was stirred at room temperature overnight
  2. washwashed with water
  3. customThe organic phase was separated
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated
  6. custompurified by chromatography

Sources & evidence

ORD record
ord-d6441a80d69f4420bb874542b8599a91
Source dataset
uspto-grants-2004_09
Patent number
US06794397B2

Reaction notes

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