Triethylamine → HCID 11587887, compound

HRID 1035101Notes

Reaction equation

HRID 1035101 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N:9]=[C:10]=O.[CH:12]1([CH2:18][NH2:19])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.[N-:20]=[N+:21]=[N-:22].[Na+].C(N(CC)CC)C>O1CCCC1.C([O-])(=O)C.[Hg+2].C([O-])(=O)C>[CH:12]1([CH2:18][NH:19][C:10]2[N:9]([C:3]3[CH:4]=[CH:5][CH:6]=[C:7]([Cl:8])[C:2]=3[Cl:1])[N:22]=[N:21][N:20]=2)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 330501,2-Dichloro-3-isocyanatobenzeneHCID 33557Sodium AzideHCID 76688Cyclohexanemethylamine

Product 1

HCID 11587887HCID 11587887, compoundYield 56.3%

Reagents, catalysts & solvents 2

HCID 15337Mercuric acetateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,3 dichlorophenylisocyanate (0.1 g, 0.49 mmol) in 5 mL anhydrous tetrahydrofuran was added cyclohexylmethylamine (0.1 g). The solution was stirred at room temperature for 2 h when mercury (II) acetate (0.13 g, 0.49 mmol), sodium azide (0.095 g, 1.47 mmol) and triethylamine (0.148 g, 1.47 mmol) were added. The resulting suspension was stirred at room temperature for 12 hours, at which time the precipitate was filtered through Celite and the organics concentrated in vacuo. The crude residue was purified by column chromatography (gradient elution; 25% ethyl acetate/hexanes to 35%) to give 0.09 g of the title compound as a sticky foam. MS (ESI/NH3) m/z 325 (M+H)+ 1H NMR (δ, DMSO-d6) 0.8-0.95 (m, 2H), 1.05-1.3 (m, 3H), 1.5-1.8 (m, 7H), 3.05-3.12 (t, 2H), 7.05-7.17 (t, 1H), 7.58-7.65 (m, 2H), 7.90-7.95 (d, 1H).

Workup

  1. additionwere added
  2. filtrationwas filtered through Celite
  3. concentrationthe organics concentrated in vacuo
  4. customThe crude residue was purified by column chromatography (gradient elution; 25% ethyl acetate/hexanes to 35%)

Sources & evidence

ORD record
ord-4c677eab244d4c8db0f37e3d645ecbd8
Source dataset
uspto-grants-2013_10
Patent number
US08546374B2

Reaction notes

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