Hydrochloric Acid → 1-Cyclopropyl-4-isothiocyanatonaphthalene

HRID 660453Notes

Reaction equation

HRID 660453 reaction equation
[C:1](Cl)(Cl)=[S:2].[NH2:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([CH:16]2[CH2:18][CH2:17]2)=[CH:8][CH:7]=1.C(N(C(C)C)CC)(C)C.Cl>ClCCl>[CH:16]1([C:9]2[C:10]3[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:6]([N:5]=[C:1]=[S:2])=[CH:7][CH:8]=2)[CH2:18][CH2:17]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10040ThiophosgeneHCID 81531DiisopropylethylamineHCID 534821124-Cyclopropylnaphthalen-1-amine

Product 1

HCID 565954581-Cyclopropyl-4-isothiocyanatonaphthaleneYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Thiophosgene (1.1 g, 9.7 mmol) was added to a stirred solution of 1-amino-4-cyclopropylnaphthalene (1.8 g, 9.7 mmol) and diisopropylethylamine (2 eq) in dichloromethane (50 mL) at 0° C. The reaction mixture was stirred for 5 min at 0° C. and then aqueous HCl (1% solution) was added. The organic layer was separated, washed with brine, dried over sodium sulfate, filtered and the solvent removed under reduced pressure. Hexane was added, and the resulting precipitate was filtered. The solvent was evaporated to yield 1-cyclopropyl-4-isothiocyanatonaphthalene (1.88 g, 86%).

Workup

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customthe solvent removed under reduced pressure
  6. additionHexane was added
  7. filtrationthe resulting precipitate was filtered
  8. customThe solvent was evaporated

Sources & evidence

ORD record
ord-a3e550cbfaf545819cae5857f39da54a
Source dataset
uspto-grants-2011_12
Patent number
US08084483B2

Reaction notes

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