Hydrochloric Acid → 1-Cyclopropyl-4-isothiocyanatonaphthalene

HRID 2061765Notes

Reaction equation

HRID 2061765 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-ad634e5876da420f937b43e8f5e94f56
Source dataset
uspto-grants-2012_10
Patent number
US08283369B2

Reaction notes

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