HCID 18002590, compound → HCID 18002593, compound

HRID 478657Notes

Reaction equation

HRID 478657 reaction equation
[O:1]=[C:2]1[N:6]([C:7]2[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][CH:8]=2)[NH:5][C:4]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:20]=3[S:21][CH2:22][C:3]1=2>CS(C)=O>[O:1]=[C:2]1[N:6]([C:7]2[CH:8]=[CH:9][C:10]([C:11]#[N:12])=[CH:13][CH:14]=2)[N:5]=[C:4]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:20]=3[S:21][CH:22]=[C:3]12

Participants

3

Reactant 1

HCID 18002590HCID 18002590, compound

Product 1

HCID 18002593HCID 18002593, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 4-(3-oxo-1,4-dihydro-3H-thiochromeno[4,3-c]pyrazol-2-yl)-benzonitrile (0.100 g, 0.33 mmol) in DMSO (2 ml) was stirred vigorously at room temperature and air was flushed over the solution. After 48 h the precipitation was filtered, washed with toluen and dried. The crude product recrystallized from toluene to yield 4-(3-oxo-3H-thiochromeno[4,3-c]pyrazol-2-yl)-benzonitrile (0.036 g): 1H NMR (400 MHz, CDCl3) δ 8.65 (1H, s), 8.53 (1H, d), 8.38 (2H, d), 7.72 (2H, d), 7.66 (2H, t), 7.58-7.62 (1H, m); ESI MS m/z 304 (M+H+).

Workup

  1. customair was flushed over the solution
  2. customAfter 48 h the precipitation
  3. filtrationwas filtered
  4. washwashed with toluen
  5. customdried
  6. customThe crude product recrystallized from toluene

Sources & evidence

ORD record
ord-11f99ee3c4e64ec9b3ce5f0ac324b157
Source dataset
uspto-grants-2003_11
Patent number
US06642249B2

Reaction notes

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