Triethylamine → 6-Chloro-N,N-bis(4-methoxybenzyl)-3-nitropyridin-2-amine

HRID 2264192Notes

Reaction equation

HRID 2264192 reaction equation
[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]([CH2:7][NH:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[CH:5][CH:4]=1.C(N(CC)CC)C.Cl[C:28]1[C:33]([N+:34]([O-:36])=[O:35])=[CH:32][CH:31]=[C:30]([Cl:37])[N:29]=1.[N-]=C=O>C(Cl)(Cl)Cl.ClCCl>[Cl:37][C:30]1[N:29]=[C:28]([N:8]([CH2:7][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:19][CH:18]=2)[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[C:33]([N+:34]([O-:36])=[O:35])=[CH:32][CH:31]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 852392,6-Dichloro-3-nitropyridineHCID 105034IsocyanateHCID 714952Bis(4-methoxybenzyl)amine

Product 1

HCID 595959876-Chloro-N,N-bis(4-methoxybenzyl)-3-nitropyridin-2-amineYield 100%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A solution of N,N-bis(4-methoxybenzyl)amine (7.79 g, 30.3 mmol) and triethylamine (2.89 g, 28.6 mmol) in chloroform (20 mL) was added dropwise over 20 minutes to a cold (ice-bath), stirred solution of 2,6-dichloro-3-nitropyridine (5.0 g, 26.0 mmol) in chloroform (25 mL). The mixture was warmed to room temperature and stirred overnight. The solvent was evaporated and the mixture was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried (MgSO4) and evaporated to give an oil. The mixture was taken up in dichloromethane (120 mL) and polymer-supported isocyanate resin (1.6 mmol/g, 8.0 g) was added and the mixture was shaken at room temperature for 2 days. The mixture was filtered and the filtrate was evaporated to give the title compound (10.7 g, 100%) as a bright yellow oil.

Workup

  1. customThe solvent was evaporated
  2. customthe mixture was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customto give an oil
  7. stirringthe mixture was shaken at room temperature for 2 days
  8. filtrationThe mixture was filtered
  9. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-7b9815ccef9644c5950575d98b885744
Source dataset
uspto-grants-2010_12
Patent number
US07855202B2

Reaction notes

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