Triethylamine → 5-Chloro-2-isocyanato-1,3-di(propan-2-yl)benzene

HRID 2303587Notes

Reaction equation

HRID 2303587 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([CH:9]([CH3:11])[CH3:10])[C:5]([NH2:6])=[C:4]([CH:12]([CH3:14])[CH3:13])[CH:3]=1.C(N(CC)CC)C.Cl[C:23](Cl)([O:25]C(=O)OC(Cl)(Cl)Cl)Cl>O1CCCC1.CCCCC>[Cl:1][C:2]1[CH:8]=[C:7]([CH:9]([CH3:10])[CH3:11])[C:5]([N:6]=[C:23]=[O:25])=[C:4]([CH:12]([CH3:14])[CH3:13])[CH:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 108891984-Chloro-2,6-diisopropylaniline

Product 1

HCID 154799605-Chloro-2-isocyanato-1,3-di(propan-2-yl)benzeneYield 279%

Reagents, catalysts & solvents 2

HCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 4-chloro-2,6-diisopropylaniline (32 grams) and triethylamine-(7.8 mL) in tetrahydrofuran (505 mL) was added triphosgene (14.9 grams). The mixture was refluxed for two hours with stirring. The tetrahydrofuran was then revolved in vacuo and the resulting oil was taken up in pentane and filtered through silica gel to afford 33.3 grams of the product. 1H NMR δ 7.18 (s, 2), 3.22 (qq, 2, J=7.1Hz), 1.25 (d, 6, J=7.1Hz), 1.25 (d, 6, J=7.1 Hz).

Workup

  1. temperatureThe mixture was refluxed for two hours
  2. filtrationfiltered through silica gel

Sources & evidence

ORD record
ord-020deb72c4a54b7787f3d7392c80d4f0
Source dataset
uspto-grants-2002_08
Patent number
US06433009B1

Reaction notes

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