Water → 4-Chloro-2-{[2-(dimethylamino)ethyl]amino}benzene-1-thiol

After removal of the solvent under reduced pressure, the residue was dissolved in ethylacetate, and the solution was washed with aqueous sodium hydroxide. The ethylacetate extract was acidified with dilute hydrochloric acid and the aqueous layer was neutralized with saturated aqueous sodium bicarbonate and then the resulting oily substance was extracted with ethylacetate. The extract was washed with water, dried (Na2SO4) and evaporated to give 5-chloro-3-(2-dimethylaminoethyl)-2-benzothiazolinone (74.5 g) as prisms. m.p. 62.5-65.5° C. 5-Chloro-3-(2-dimethylaminoethyl)-2-benzothiazolinone (74.5 g) was added to a mixture of water (110 ml), ethanol (350 ml) and potassium hydroide (75.0 g). The solution was refluxed with stirring for two hours. After removal of the solvent under reduced pressure, the residual oil was dissolved in water, then the aqueous solution was washed with ether. The aqueous layer was washed and neutralized with 2N-acetic acid with weak stirring. The resulting light yellow precipitates were collected on a filter, washed with water and air-dried to give 4-chloro-2-(2 -dimethylaminoethylamino)-thiophenol (52.9 g) as prisms. m.p. 126-130° C.

1. temperatureThe solution was refluxed
2. customAfter removal of the solvent under reduced pressure
3. dissolutionthe residual oil was dissolved in water
4. washthe aqueous solution was washed with ether
5. washThe aqueous layer was washed
6. customThe resulting light yellow precipitates
7. customwere collected on a filter
8. washwashed with water
9. customair-dried

ORD record

ord-29f7d9411b8c4182889b360c654197f1

Source dataset

uspto-grants-1984_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04490292