Toluene → HCID 178455365, compound

HRID 2216998Notes

Reaction equation

HRID 2216998 reaction equation
[C:1]([Si:5]([CH3:15])([CH3:14])[O:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([NH2:13])[CH2:9][CH2:8]1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:23](Cl)(Cl)=[O:24].C1(C)C=CC=CC=1>ClCCl>[C:1]([Si:5]([CH3:15])([CH3:14])[O:6][C@H:7]1[CH2:8][CH2:9][C@H:10]([N:13]=[C:23]=[O:24])[CH2:11][CH2:12]1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 1140TolueneHCID 6371PhosgeneHCID 8471TriethylamineHCID 178455364HCID 178455364, compound

Product 1

HCID 178455365HCID 178455365, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of trans-4-(tert-butyl-dimethyl-silanyloxy)-cyclohexylamine (500 mg, 2.20 mmol) (from Example 20a supra) and triethylamine (1.52 mL, 10.90 mmol) (Aldrich) in dichloromethane (15 mL) was added a 20% phosgene in toluene solution (3.2 mL, 6.50 mmol) (Fluka) at 0° C. The resulting mixture was stirred for 15 minutes, then filtered and the filtrate was concentrated to a residue that was distilled at 110° C. under high vacuum using a Kugelrohr apparatus to give trans-4-(tert-butyl-dimethyl-silanyloxy)-cyclohexyl isocyanate (485 mg) as a colorless liquid.

Workup

  1. filtrationfiltered
  2. concentrationthe filtrate was concentrated to a residue that
  3. distillationwas distilled at 110° C. under high vacuum

Sources & evidence

ORD record
ord-7ace4f78998141859d55d04692ea6754
Source dataset
uspto-grants-2006_09
Patent number
US07112676B2

Reaction notes

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