Accelerator DM → 2-Hydroxyethyl dithiobenzthiazole

HRID 370124

Reaction equation

HRID 370124 reaction equation
ClCl.[S:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[C:4]1[S:12][S:13][C:14]1SC2C=CC=CC=2N=1.S[CH:24]([OH:26])C>ClC1C=CC=CC=1>[OH:26][CH2:24][CH2:14][S:13][S:12][C:4]1[S:3][C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=1

Participants

5

Reactant 3

HCID 8447Accelerator DMHCID 24526ChlorineHCID 4713212Mercapto-ethanol

Product 1

HCID 102435162-Hydroxyethyl dithiobenzthiazoleYield 167.6%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

Chlorine gas (17.5 g/0.25 mole) was passed at 0 to 50C into a suspension of 2,2'-dithiobisbenzthiazole (83 g/0.25 mole) in chlorobenzene (600 ml). Mercaptoethanol (39 g/0.5 mole) was then added drop-wise to this solution, followed by stirring for 7 hours at room temperature. The precipitated product was filtered off, mixed with methylene chloride (500 ml) and washed with 5% NaHCO3 solution (500 ml). The organic phase was concentrated by evaporation. A yellowish-brown oil (102 g) was obtained, which crystallised after a short time. m.pt.: 65 to 68° C.

Workup

  1. filtrationThe precipitated product was filtered off
  2. additionmixed with methylene chloride (500 ml)
  3. washwashed with 5% NaHCO3 solution (500 ml)
  4. concentrationThe organic phase was concentrated by evaporation

Sources & evidence

ORD record
ord-98ea8cec25a647919a536e0861275368
Source dataset
uspto-grants-2000_10
Patent number
US06140427

Linked notes

Loading…