Triethylamine → 1-Cyclopropyl-4-isothiocyanatonaphthalene

HRID 2245594Notes

Reaction equation

HRID 2245594 reaction equation
O[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[C:9]2[NH:12]C(=O)OC(C)(C)C)=[CH:4][CH:3]=1.C(N([CH2:25][CH3:26])CC)C.CS(O[S:32]([CH3:35])(=O)=O)(=O)=O.[C:36](=O)(O)[O-].[Na+]>ClCCl>[CH:26]1([C:6]2[C:5]3[C:10](=[CH:11][CH:2]=[CH:3][CH:4]=3)[C:9]([N:12]=[C:35]=[S:32])=[CH:8][CH:7]=2)[CH2:25][CH2:36]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 81560Methanesulfonic anhydrideHCID 516892Sodium BicarbonateHCID 18536180tert-Butyl (7-hydroxynaphthalen-1-yl)carbamate

Product 1

HCID 565954581-Cyclopropyl-4-isothiocyanatonaphthaleneYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2 (12.36 g, 47.7 mmol) and triethylamine (9.97 mL, 71.5 mmol) in dichloromethane (400 mL) was added methanesulfonic anhydride (9.3 g, 52.4 mmol) at 0° C. The mixture was stirred for 30 min and poured into saturated aqueous sodium bicarbonate solution. The organic layer was extracted with dichloromethane, dried over sodium sulfate, filtered and concentrated under reduced pressure to give 8-tert-butoxycarbonylamino)naphthalen-2-yl methanesulfonate (3). (14.85 g, 92% yield)

Workup

  1. extractionThe organic layer was extracted with dichloromethane
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7cac0f2af3b4418789ad17d86cb45f10
Source dataset
uspto-grants-2010_03
Patent number
US07683087B2

Reaction notes

Loading…