Hydrochloric Acid → S,N-dimethyl-N'-nitro-N-trichloromethanesulfenylisothiourea

To a cooled, stirred mixture of S,N-dimethyl-N'-nitroisothiourea (1.0 g), triethylamine (0.68 g) and DMF (10 ml) was added 1.2 g of trichloromethanesulfenyl chloride dropwise at 3°-7° C. After stirring at the same temperature for 1 hour, the mixture was poured into 50 ml of 2N hydrochloric acid and the resulting mixture was extracted with toluene (50 ml). The toluene layer was washed with water (50 ml), dried over MgSO4 and concentrated in vacuo. The resulting residue was applied to column chromatography on silica gel. The column was eluted with hexane-AcOEt (8:1). The fractions containing the desired product were concentrated to afford 1.1 g of S,N-dimethyl-N'-nitro-N-trichloromethanesulfenylisothiourea as a pale yellow crystal, m.p. 75°-78° C.

1. stirringAfter stirring at the same temperature for 1 hour
2. extractionthe resulting mixture was extracted with toluene (50 ml)
3. washThe toluene layer was washed with water (50 ml)
4. dry with materialdried over MgSO4
5. concentrationconcentrated in vacuo
6. washThe column was eluted with hexane-AcOEt (8:1)
7. additionThe fractions containing the desired product
8. concentrationwere concentrated

ORD record

ord-341e08c05c364c8098613c4433a8f977

Source dataset

uspto-grants-1993_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05256679