Hydrochloric Acid → 6-Chloro-3-fluoro-4H-thieno[3,2-e]-1,2,4-thiadiazine 1,1-dioxide

HRID 2268744Notes

Reaction equation

HRID 2268744 reaction equation
Cl[C:2]1[NH:7][C:6]2[CH:8]=[C:9]([Cl:11])[S:10][C:5]=2[S:4](=[O:13])(=[O:12])[N:3]=1.[F-:14].[Cs+].O.Cl>CS(C)=O>[Cl:11][C:9]1[S:10][C:5]2[S:4](=[O:13])(=[O:12])[N:3]=[C:2]([F:14])[NH:7][C:6]=2[CH:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 25953Cesium fluorideHCID 118320583,6-Dichloro-4h-thieno[3,2-e][1,2,4]thiadiazine 1,1-dioxide

Product 1

HCID 109226916-Chloro-3-fluoro-4H-thieno[3,2-e]-1,2,4-thiadiazine 1,1-dioxideYield 80.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
155 °C

Procedure

A mixture of 3,6-dichloro-4H-thieno[3,2-e]-1,2,4-thiadiazine 1,1-dioxide (257 mg, 1.0 mmol) and cesium fluoride (456 mg, 3.0 mmol) in dry DMSO (1 ml) was stirred for 16 h at 155° C. in a sealed flask. Water (3 ml) was added to the cooled mixture followed by 4M hydrochloric acid to pH <2. The precipitated beige solid was isolated by filtration, washed with water and dried to give 193 mg (80%) of the title compound; 1H-NMR (DMSO-d6): δ7.09 (s, 1H), 7.34 (br s, 1H; MS: m/e 240/242 (M+).

Workup

  1. customThe precipitated beige solid was isolated by filtration
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-713a9809778d4a4694fefad9ebe3c6c5
Source dataset
uspto-grants-2001_12
Patent number
US06329367B1

Reaction notes

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