Benzenamine, N-sulfinyl- → 4-Fluoro-2,1,3-benzothiadiazole

HRID 2400262Notes

Reaction equation

HRID 2400262 reaction equation
[S:1](=NC1C=CC=CC=1)=O.[CH:10]1[CH:15]=[C:14]([F:16])[C:13]([NH2:17])=[C:12]([NH2:18])[CH:11]=1>>[F:16][C:14]1[C:13]2[C:12](=[N:18][S:1][N:17]=2)[CH:11]=[CH:10][CH:15]=1

Participants

3

Reactant 2

HCID 70739Benzenamine, N-sulfinyl-HCID 27828353-Fluorobenzene-1,2-diamine

Product 1

HCID 157174614-Fluoro-2,1,3-benzothiadiazole

Conditions

Temperature
110 °C

Procedure

4-Fluoro-2,1,3-benzothiadiazole was synthesized according to the method in which N-thionylaniline (0.49 g, 3.5 mmol) was added to a solution of the 3-fluoro-O-phenylene diamine (200 mg, 1.6 mmol) in foluen (2 ml) The reaction mixture was heated at 100-120° C. for 4 hr. After the solvent was filtered off, the residue was dissolved in dichloromethane and the solution was washed with 10% HCl solution and water, successively. The organic layer was dried and evaporated to dryness. Purification by chromatography on a silica gel column with chloroform as an eluent gave 4-fluoro-2,1,3-benzothiadiazole as pal yellow oil. Confirmed data of the obtained chemical compound is shown as follows.

Workup

  1. custom4-Fluoro-2,1,3-benzothiadiazole was synthesized
  2. filtrationAfter the solvent was filtered off
  3. dissolutionthe residue was dissolved in dichloromethane
  4. washthe solution was washed with 10% HCl solution and water
  5. customThe organic layer was dried
  6. customevaporated to dryness
  7. customPurification by chromatography on a silica gel column with chloroform as an eluent

Sources & evidence

ORD record
ord-a8158a7d3c5d48899f27b304a56fbc76
Source dataset
uspto-grants-2014_08
Patent number
US08796037B2

Reaction notes

Loading…