Triethylamine → (2-Chloro-3-nitro-6-trifluoromethyl-pyridin-4-yl)-carbamic acid ethyl ester

HRID 639629Notes

Reaction equation

HRID 639629 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([NH2:11])[CH:5]=[C:4]([C:12]([F:15])([F:14])[F:13])[N:3]=1.C(N(CC)CC)C.Cl[C:24]([O:26][CH2:27][CH3:28])=[O:25].CCOC(C)=O>CC1OCCC1>[CH2:27]([O:26][C:24](=[O:25])[NH:11][C:6]1[CH:5]=[C:4]([C:12]([F:13])([F:14])[F:15])[N:3]=[C:2]([Cl:1])[C:7]=1[N+:8]([O-:10])=[O:9])[CH3:28]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 10928Ethyl chloroformateHCID 866144742-Chloro-3-nitro-6-trifluoromethyl-pyridin-4-ylamine

Product 1

HCID 86614475(2-Chloro-3-nitro-6-trifluoromethyl-pyridin-4-yl)-carbamic acid ethyl esterYield 73.6%

Reagents, catalysts & solvents 1

HCID 73012-MethyltetrahydrofuranSolvent

Procedure

2-Chloro-3-nitro-6-trifluoromethyl-pyridin-4-ylamine (2.2 g, 9.1 mmol) was stirred in 2-MeTHF (20 ml) and triethylamine added (1.52 ml, 10.9 mmol). The solution was cooled in an ice bath to ˜5° C. before the dropwise addition of ethyl chloroformate (1.04 ml, 10.9 mmol), the solution warmed to ambient temperature and left to stir under a nitrogen atmosphere for 16 h. 20 ml EtOAc and 10 ml H20 were added and the phases separated, washed with a additional 2×10 ml sat'd brine solution. The organic extract was dried over MgSO4, concentrated in vacuo and preabsorbed onto a silica column. Elution with Hept:EtOAc, 9:1 gave 2.1 g of the title compound as a white solid.

Workup

  1. waitleft
  2. customthe phases separated
  3. washwashed with a additional 2×10 ml
  4. extractionThe organic extract
  5. dry with materialwas dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. custompreabsorbed onto a silica column
  8. washElution with Hept

Sources & evidence

ORD record
ord-893740c733744b95a28748a0665b2b6f
Source dataset
uspto-grants-2010_04
Patent number
US07691877B2

Reaction notes

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