Thiophosgene → 1-Cyclopropyl-4-isothiocyanatonaphthalene

HRID 425302Notes

Reaction equation

HRID 425302 reaction equation
[CH:1]1([C:4]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7]([NH2:14])=[CH:6][CH:5]=2)[CH2:3][CH2:2]1.C(=O)(O)[O-].[Na+].[C:20](Cl)(Cl)=[S:21]>ClCCl>[CH:1]1([C:4]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7]([N:14]=[C:20]=[S:21])=[CH:6][CH:5]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 10040ThiophosgeneHCID 516892Sodium BicarbonateHCID 534821124-Cyclopropylnaphthalen-1-amine

Product 1

HCID 565954581-Cyclopropyl-4-isothiocyanatonaphthaleneYield 149.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 2 (440 mg, 2.6 mmol) was dissolved in 14 mL of dichloromethane. Sodium bicarbonate (7 mL, sat. solution) and thiophosgene (0.2 mL, 2.6 mmol) were added and the mixture stirred at room temperature for 1 h. Then, the organic layer was separated, dried over sodium sulfate and concentrated to afford 877 mg, 99% yield of 1-cyclopropyl-4-isothiocyanatonaphthalene (3) which was used in the next step without further purification

Workup

  1. customThen, the organic layer was separated
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-c66ed7c310394380a808e8ed50831800
Source dataset
uspto-grants-2012_01
Patent number
US08106205B2

Reaction notes

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