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

HRID 501512

Reaction equation

HRID 501512 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-d93fd10229394289bffabb38e613fd6d
Source dataset
uspto-grants-2010_08
Patent number
US07772267B2

Linked notes

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