Thionyl Chloride → 2-Chloro-6-(trifluoromethoxy)-1,3-benzothiazole

HRID 865795

Reaction equation

HRID 865795 reaction equation
N([C:3]1[S:4][C:5]2[CH:11]=[C:10]([O:12][C:13]([F:16])([F:15])[F:14])[CH:9]=[CH:8][C:6]=2[N:7]=1)N.S(Cl)([Cl:19])=O>>[Cl:19][C:3]1[S:4][C:5]2[CH:11]=[C:10]([O:12][C:13]([F:16])([F:15])[F:14])[CH:9]=[CH:8][C:6]=2[N:7]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 104221582-Hydrazinyl-6-(trifluoromethoxy)-1,3-benzothiazole

Product 1

HCID 100379242-Chloro-6-(trifluoromethoxy)-1,3-benzothiazole

Conditions

Temperature
50 °C

Procedure

49.4 g of 2-hydrazino-6-trifluoromethoxybenzothiazole are added over one hour to 97.9 g of thionyl chloride heated to 50° C. The mixture is then heated for one hour at this same temperature and then cooled to 0° C. After addition of 200 g of an ice/water mixture (1/1 by weight), the precipitate is filtered off and washed with twice 50 cm3 of water. 54.5 g of 2-chloro-6-trifluoromethoxybenzothiazole are thus obtained, melting at 50° C.

Workup

  1. temperatureThe mixture is then heated for one hour at this same temperature
  2. temperaturecooled to 0° C
  3. filtrationthe precipitate is filtered off
  4. washwashed with twice 50 cm3 of water

Sources & evidence

ORD record
ord-e6e2b4ad6f8e4edbb743a4d33e7773fe
Source dataset
uspto-grants-1996_10
Patent number
US05567822

Linked notes

Loading…