Chloroform → 2-(Naphthalen-1-yl)acetyl chloride

1-Naphthylacetyl chloride is prepared according to the method described in Example 8 using 1-naphthylacetic acid (2.0 g, 10.8 mmol) to give a yellow oil which is dissolved in chloroform (10 mL). This solution is added to a solution of (±)-trans-[2-(4-morpholinyl)]cyclohexanethiol (2 g, 10 mmol) in chloroform (10 mL), and the mixture is stirred at room temperature for 8 hours under nitrogen. The solvent is removed and the residue is partitioned between 1M hydrochloric acid (100 mL) and ether (80 mL). The organic layer is separated and the aqueous is washed with more ether (2×60 mL). The aqueous mixture is basified to pH>12 by the addition of 50% sodium hydroxide solution, and extracted with ether (1×80 mL, 2×50 mL). These ether extracts of the basic aqueous solution are washed repeatedly with water to remove any unreacted aminothiol, dried over sodium sulfate, and the solvent is removed to leave the crude free thioester. This is converted to the hydrochloride salt by dissolving it in 1M hydrochloric acid (60 mL), adding sodium chloride (12 g), and extracting with chloroform (3×75 mL). The chloroform is removed in vacuo and the residue is recrystallised from ethyl acetate/methanol to yield the title compound.

1. customto give a yellow oil which
2. customThe solvent is removed
3. customthe residue is partitioned between 1M hydrochloric acid (100 mL) and ether (80 mL)
4. customThe organic layer is separated
5. washthe aqueous is washed with more ether (2×60 mL)
6. additionThe aqueous mixture is basified to pH>12 by the addition of 50% sodium hydroxide solution
7. extractionextracted with ether (1×80 mL, 2×50 mL)
8. washThese ether extracts of the basic aqueous solution are washed repeatedly with water
9. customto remove any unreacted aminothiol
10. dry with materialdried over sodium sulfate
11. customthe solvent is removed
12. customto leave the crude free thioester

ORD-Eintrag

ord-ee1317848d3b468d8f32bcbe3a336ae1

Quelldatensatz

uspto-grants-2001_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06174879B1