Ethanethiol → 10-Ethylsulfanyl-1,8-dihydroxy-10H-anthracen-9-one

HRID 1651142Notes

Reaction equation

HRID 1651142 reaction equation
Br[CH:2]1[C:15]2[C:10](=[C:11]([OH:16])[CH:12]=[CH:13][CH:14]=2)[C:9](=[O:17])[C:8]2[C:7]([OH:18])=[CH:6][CH:5]=[CH:4][C:3]1=2.[CH2:19]([SH:21])[CH3:20]>ClCCl>[OH:18][C:7]1[C:8]2[C:9](=[O:17])[C:10]3[C:15](=[CH:14][CH:13]=[CH:12][C:11]=3[OH:16])[CH:2]([S:21][CH2:19][CH3:20])[C:3]=2[CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 6343EthanethiolHCID 27650410-Bromo-1,8-dihydroxy-10H-anthracen-9-one

Product 1

HCID 2006726210-Ethylsulfanyl-1,8-dihydroxy-10H-anthracen-9-oneYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

10-Bromo-1,8-dihydroxy-9-anthrone (3.05 g) was dissolved in dichloromethane (100 ml) and ethanethiol (1 ml) was added. The solution was left stirring at room temperature for 6 hours, during which time the red-brown solution became yellow-green. Removal of the solvent gave a yellow solid which, recrystallised from hexane, gave 1,8-dihydroxy-10-ethylthio-9-anthrone (2.63 g, 91%) as bright yellow needles, melting point 117°-118° C. (Found: C 67.3, H 5.1, S 11.1; C16H14O3S requires C 67.1, H 4.93, S 11.2%.)

Workup

  1. waitThe solution was left
  2. customRemoval of the solvent
  3. customgave a yellow solid which
  4. customrecrystallised from hexane

Sources & evidence

ORD record
ord-ce3e5d78052b46e7b5103cf20dca71f5
Source dataset
uspto-grants-1990_05
Patent number
US04927845

Reaction notes

Loading…