Thiophosgene → 1-Cyclopropyl-4-isothiocyanatonaphthalene

HRID 889405Notes

Reaction equation

HRID 889405 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-8aa0678888214bcfac9a114751f459f5
Source dataset
uspto-grants-2012_08
Patent number
US08252828B2

Reaction notes

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