Aniline → 1-(Benzo[c][1,2,5]thiadiazol-5-yl)propan-1-one

HRID 626236Notes

Reaction equation

HRID 626236 reaction equation
NC1C=CC=CC=1.O=[S:9](Cl)Cl.[NH2:12][C:13]1[CH:14]=[C:15]([C:20](=[O:23])[CH2:21][CH3:22])[CH:16]=[CH:17][C:18]=1[NH2:19]>C1(C)C=CC=CC=1>[N:19]1[S:9][N:12]=[C:13]2[CH:14]=[C:15]([C:20](=[O:23])[CH2:21][CH3:22])[CH:16]=[CH:17][C:18]=12

Participants

5

Reactant 3

HCID 6115AnilineHCID 24386Thionyl ChlorideHCID 202165581-(3,4-Diaminophenyl)propan-1-one

Product 1

HCID 896575531-(Benzo[c][1,2,5]thiadiazol-5-yl)propan-1-oneYield 50%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of aniline (1.86 g, 20 mmol) in 50 mL of toluene was added SOCl2 (2.6 g, 22 mmol) dropwise at 0° C. and the mixture was then refluxed for 2 h. After cooling to rt, 1-(3,4-diaminophenyl)propan-1-one (1.65 g, 10 mmol) was added. The mixture was refluxed for 2 h, cooled, concentrated, and purified by flash chromatography to give the desired product (960 mg, 50%) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ 8.62 (s, 1H), 8.21 (d, J=9.2 Hz, 1H), 8.06 (d, J=9.2 Hz, 1H), 3.15 (q, J=7.2 Hz, 2H), 1.30 (t, J=7.2 Hz, 3H).

Workup

  1. temperaturethe mixture was then refluxed for 2 h
  2. temperatureThe mixture was refluxed for 2 h
  3. temperaturecooled
  4. concentrationconcentrated
  5. custompurified by flash chromatography

Sources & evidence

ORD record
ord-3ca546ba55c9426c85daa1b8c54f3332
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

Loading…