Toluene → 4-Isocyanato-5,6,7,8-tetrahydronaphthalene-1-carbonitrile

HRID 751032Notes

Reaction equation

HRID 751032 reaction equation
Cl.[NH2:2][C:3]1[C:12]2[CH2:11][CH2:10][CH2:9][CH2:8][C:7]=2[C:6]([C:13]#[N:14])=[CH:5][CH:4]=1.[C:15]([O-])(O)=[O:16].[Na+].C(Cl)(Cl)=O.C1(C)C=CC=CC=1>C(Cl)Cl>[N:2]([C:3]1[C:12]2[CH2:11][CH2:10][CH2:9][CH2:8][C:7]=2[C:6]([C:13]#[N:14])=[CH:5][CH:4]=1)=[C:15]=[O:16]

Participants

6

Reactant 4

HCID 1140TolueneHCID 6371PhosgeneHCID 516892Sodium BicarbonateHCID 1317269774-Amino-5,6,7,8-tetrahydronaphthalene-1-carbonitrile, hydrochloride salt

Product 1

HCID 597543044-Isocyanato-5,6,7,8-tetrahydronaphthalene-1-carbonitrileYield 99.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirring suspension of compound 2D (0.10 g, 0.48 mmol) and NaHCO3 (0.404 g, 4.80 mmol) in CH2Cl2 (4 mL) cooled to 0° C. was rapidly added a solution of phosgene (20%) in toluene (0.95 mL, 4.32 mmol). After addition, the mixture was stirred at rt for 2 h, then filtered to remove the solid. The filtrate was concentrated under reduced pressure, the resulting solid residue dried under vacuum for 1 h to afford compound 2E (95 mg) as a light yellow solid.

Workup

  1. additionAfter addition
  2. filtrationfiltered
  3. customto remove the solid
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe resulting solid residue dried under vacuum for 1 h

Sources & evidence

ORD record
ord-a2594cde4d574c4e9beadfb06dae6fd6
Source dataset
uspto-grants-2008_07
Patent number
US07405234B2

Reaction notes

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