Bromine → HCID 178456992, compound

HRID 1975928Notes

Reaction equation

HRID 1975928 reaction equation
[Br:1]Br.Cl[C:4]1[S:12][C:11]2[S:10](=[O:14])(=[O:13])[N:9]=[C:8]([NH:15][CH:16]([CH3:18])[CH3:17])[NH:7][C:6]=2[CH:5]=1>C(O)(=O)C>[Br:1][C:4]1[S:12][C:11]2[S:10](=[O:14])(=[O:13])[N:9]=[C:8]([NH:15][CH:16]([CH3:18])[CH3:17])[NH:7][C:6]=2[CH:5]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 1784569956-chloro-1,1-dioxo-N-propan-2-yl-4H-thieno[3,2-e][1,2,4]thiadiazin-3-amine

Product 1

HCID 178456992HCID 178456992, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

Bromine (0.12 ml, 2.3 mmol) was added dropwise to a solution of 6-chloro-3-isopropylamino-4H-thieno[3,2-e]-1,2,4-thiadiazine 1,1-dioxide (280 mg, 1.0 mmol) in 10 ml of acetic acid and the mixture was stirred for 24 h at 100° C. in a sealed flask. The cooled mixture was evaporated to dryness and the residue was triturated with water to give a solid, which was recrystallised from ethanol/water (1:1) affording 118 mg (39%) of the title compound contaminated with 10% of the starting material; mp ca. 279° C. (aqueous ethanol); 1H-NMR (DMSO-d6): δ1.16 (d, 6H, 2×CH3), 3.86 (m, 1H, CH), 7.14 (s, 1H, H-5), 7.18 (br, 1H, NH), 10.74 (s, 1H, NH); MS: m/e 323/325 (M+).

Workup

  1. customThe cooled mixture was evaporated to dryness
  2. customthe residue was triturated with water
  3. customto give a solid, which
  4. customwas recrystallised from ethanol/water (1:1)

Sources & evidence

ORD record
ord-95b8b214a2594302944750b64871b082
Source dataset
uspto-grants-2001_05
Patent number
US06225310B1

Reaction notes

Loading…