Bromine → HCID 178456992, compound

Participants

Reaction Conditions

Reaction Steps

Bromine (1.26 ml, 25 mmol) was added dropwise to a solution of 6-chloro-3-isopropylamino-4H-thieno[3,2-e]-1,2,4-thiadiazine 1,1-dioxide (2.3 g, 8.2 mmol) in 25 ml of acetic acid and the mixture was stirred for 48 h at 100° C. in a sealed flask. The cooled mixture was evaporated to dryness and the residue which consisted of two major products was triturated with water to give a solid, which was recrystallised from ethyl acetate/methanol with decolorising charcoal to afford 538 mg (20%) of the title compound. An analytically pure sample was obtained by preparative hplc on a Source RPC 15 column using acetonitrile/water (20:80) with 0.1% TFA as eluent; mp 282-283° C.; 1H-NMR (DMSO-d6): δ1.16 (d, 6H), 3.86 (m, 1H), 7.14 (s, 1H), 7.18 (br, 1H), 10.74 (s, 1H); MS: m/e 323/325 (M+); (C8H10N3Br1O2S2); calc C, 29.64; H, 3.11; N, 12.96; found C, 29.49; H, 3.04; N, 12.59.

Provenance & Evidence