Thianthrene → Chlorothianthrene

HRID 1729705Notes

Reaction equation

HRID 1729705 reaction equation
[CH:1]1[C:14]2[S:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[S:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[Cl:15]Cl>ClC1C=CC(C)=CC=1>[Cl:15][C:11]1[C:12]2[S:13][C:14]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[S:6][C:7]=2[CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 7109ThianthreneHCID 24526Chlorine

Product 1

HCID 22624821Chlorothianthrene

Reagents, catalysts & solvents 1

HCID 78104-ChlorotolueneSolvent2×

Procedure

Twenty parts of thianthrene dissolved in 142 parts of monochlorotoluene (a commercial mixture of about 50 percent ortho- and 50 percent para-chlorotoluene) were charged to a batch type stirred tank reactor together with 0.2 part of SbCl3. Chlorine was fed to the reaction mixture at about 0.35 parts/min. for a 4 hour period. The mixture was then cooled and 14.5 parts of chlorothianthrene were obtained which had 68.03 percent 2,3,7,8 -tetrachlorothianthrene. Part of this sample was recrystallized from tetrahydrofuran to produce 95.3 percent 2,3,7,8-tetrachlorothianthrene, melting point 250°-255° C. Another 3.7 parts were recovered as a second crop from the mother liquor, giving a total yield of 19.2 parts of chlorothianthrene. This second crop was low melting with 43.25 percent of the 2,3,7,8 -isomer indicating that the composition was a mixture of 2-chloro-, 2,7-dichloro-, and other isomers with 2,3,7,8-tetrachlorothianthrene.

Workup

  1. additionwere charged to a batch type
  2. temperatureThe mixture was then cooled

Sources & evidence

ORD record
ord-514b3b3c1165410b96fb30ef7c7fc613
Source dataset
uspto-grants-1976_11
Patent number
US03989715

Reaction notes

Loading…