Hydrochloric Acid → 2(3H)-Benzothiazolethione, 6,7-dichloro-

HRID 598514Notes

Reaction equation

HRID 598514 reaction equation
[Cl:1][C:2]1[C:3](F)=[C:4]([CH:6]=[CH:7][C:8]=1[Cl:9])[NH2:5].CCO[C:14]([S-:16])=[S:15].[K+].Cl>CN(C)C=O.O>[Cl:9][C:8]1[CH:7]=[CH:6][C:4]2[N:5]=[C:14]([SH:16])[S:15][C:3]=2[C:2]=1[Cl:1]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 2735045Potassium ethylxanthateHCID 27827033,4-Dichloro-2-fluoroaniline

Product 1

HCID 1785277912(3H)-Benzothiazolethione, 6,7-dichloro-Yield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 1.5 g (8.33 mmol) 3.4-dichloro-2-fluoroaniline and 1.64 g (10.00 mmol) potassium ethylxanthogenate in 8 mL dry N,N-dimethylformamide was heated in a 95° C. oil bath for 5 h. The reaction mixture was cooled to room temperature and diluted with water (25 mL). The mixture was acidified with aqueous HCl 2N. The precipitate was collected by filtration, washed with water and dried to provide 1.8 g (92%) of the title compound as a white solid. MS(m/e): 233.8 (M−H+).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-88f96fc5bfa742dfbcd4c125c62a6cc8
Source dataset
uspto-grants-2011_03
Patent number
US07897627B2

Reaction notes

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