Hydrochloric Acid → 1-Cyclopropyl-4-isothiocyanatonaphthalene

HRID 1675475Notes

Reaction equation

HRID 1675475 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.O>[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

7

Reactant 4

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

Product 1

HCID 565954581-Cyclopropyl-4-isothiocyanatonaphthaleneYield 86%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Thiophosgene (1.1 g, 9.7 mmol) was added to a solution of 1-amino-4-cyclopropyl-naphthalene (1.8 g, 9.7 mmol) and diisopropylethylamine (2 eq) in dichloromethane (50 mL) stirred at 0° C. The reaction mixture was stirred for 5 min at this temperature, then a 1% solution of HCl in water was added and the organic layer was separated, washed with brine, dried over sodium sulfate, filtered and the solvent was evaporated 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. stirringThe reaction mixture was stirred for 5 min at this temperature
  2. customthe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customthe solvent was evaporated under reduced pressure
  7. additionHexane was added
  8. filtrationthe resulting precipitate was filtered
  9. customThe solvent was evaporated

Sources & evidence

ORD record
ord-ea40d305859c4fcab4549382122b6553
Source dataset
uspto-grants-2011_08
Patent number
US08003681B2

Reaction notes

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