Toluene → Tetradecyl isocyanate

HRID 479914Notes

Reaction equation

HRID 479914 reaction equation
[CH2:1]([NH2:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[C:16](=O)(O)[O-:17].[K+].C(Cl)(Cl)=O.C1(C)C=CC=CC=1>C(Cl)Cl.O>[CH2:1]([N:15]=[C:16]=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

7

Reactant 4

HCID 1140TolueneHCID 6371PhosgeneHCID 16217TetradecylamineHCID 516893Potassium Bicarbonate

Product 1

HCID 3485710Tetradecyl isocyanate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a vigorously-stirred, biphasic mixture of 1-tetradecylamine (9.44 g, 44.2 mmol) in CH2Cl2 (300 mL) and potassium bicarbonate (21.8 g, 158 mmol) in H2O (200 mL) was added (dropwise) a 1.93 M solution of phosgene in toluene (30.0 mL, 57.9 mmol) at 0° C. After 30 min, the organic layer was separated and dried over MgSO4. The volatile components were removed with a rotary evaporator to afford crude tetradecyl isocyanate which was immediately taken up in THF (15 mL) and added to a heterogeneous mixture of 5,6-dichlorobenzotriazole (5.94 g, 31.6 mmol) and THF (125 mL). The reaction mixture was stirred at ambient temperature for 14 h, and the volatile components were then removed with a rotary evaporator. The crude product was first purified by silica gel column chromatography (heptane: ethyl acetate=7:3) and then recrystallized from ethanol to afford 12.2 g (90%) of D12.

Workup

  1. customthe organic layer was separated
  2. dry with materialdried over MgSO4
  3. customThe volatile components were removed with a rotary evaporator

Sources & evidence

ORD record
ord-79800fdcd76d4d788696578590213f3a
Source dataset
uspto-grants-2003_11
Patent number
US06649332B2

Reaction notes

Loading…