Benzene → HCID 86596158, compound

HRID 1926564Notes

Reaction equation

HRID 1926564 reaction equation
[C:1]([N:3]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[CH:9]2)=[C:4]1[C:12]1[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][CH:13]=1)#[N:2].C1C=CC=CC=1.C(N(CC)CC)C.[C:32](Cl)(Cl)=[S:33]>O1CCCC1>[C:1]([N:3]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[CH:9]2)=[C:4]1[C:12]1[CH:18]=[CH:17][C:15]([N:16]=[C:32]=[S:33])=[CH:14][CH:13]=1)#[N:2]

Participants

6

Reactant 4

HCID 241BenzeneHCID 8471TriethylamineHCID 10040ThiophosgeneHCID 23019728HCID 23019728, compound

Product 1

HCID 86596158HCID 86596158, compoundYield 38.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

84 mg (0.36 mmol) of 4-(2′-cyanoisoindolyl)aniline was suspended in 40 mL of a mixture of benzene and tetrahydrofuran (1:1, v/v) and refluxed for 1 hour in the presence of 65 mg (0.64 mmol) of triethylamine and 40 mg (0.35 mmol) of thiophosgene. The reaction mixture was concentrated under a vacuum, and then the residue was recrystallized with acetonitrile to obtain 37 mg of the titled 4-(2′-cyanoisoindolyl)phenylisothiocyanate expressed by the following formula in the form of a colorless needle crystal.

Workup

  1. concentrationThe reaction mixture was concentrated under a vacuum
  2. customthe residue was recrystallized with acetonitrile

Sources & evidence

ORD record
ord-53cd11d598454faaa9eee88e90bf0b4e
Source dataset
uspto-grants-2012_05
Patent number
US08183060B2

Reaction notes

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