Pyridine → HCID 21569121, compound

HRID 1579842Notes

Reaction equation

HRID 1579842 reaction equation
[SH:1][CH:2]([C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:16][CH3:17])[CH:12]=2)[CH:7]=1)[C:3]([OH:5])=[O:4].N1C=CC=CC=1.Cl[C:25]([O:27][CH2:28][CH3:29])=[O:26]>CCOCC>[CH2:28]([O:27][C:25]([S:1][CH:2]([C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:16][CH3:17])[CH:12]=2)[CH:7]=1)[C:3]([OH:5])=[O:4])=[O:26])[CH3:29]

Participants

5

Reactant 3

HCID 1049PyridineHCID 10928Ethyl chloroformateHCID 21569107HCID 21569107, compound

Product 1

HCID 21569121HCID 21569121, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of α-mercapto-6-methoxy-2-naphthylacetic acid (0.02 moles) in 25 ml. of pyridine is cooled in an ice bath. To this is added dropwise 2.1 mol (0.022 moles) of ethyl chloroformate. The mixture is then stirred for 2 hours, diluted with ether and filtered. The mixture is basified with 10% sodium bicarbonate solution. The alkaline mixture is worked with ether, then acidified with 10% hydrochloric acid, washed with ether, dried and filtered. The solvent is removed and the residue is triturated with hexane to obtain α-ethoxycarbonylthio-6-methoxy-2-naphthylacetic acid.

Workup

  1. filtrationfiltered
  2. washwashed with ether
  3. customdried
  4. filtrationfiltered
  5. customThe solvent is removed
  6. customthe residue is triturated with hexane

Sources & evidence

ORD record
ord-0697f90b8eb744779fbe2a74adc098d8
Source dataset
uspto-grants-1976_01
Patent number
US03931269

Reaction notes

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