P-Toluenesulfonylhydrazide → HCID 89760726, compound

HRID 1479153Notes

Reaction equation

HRID 1479153 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[C:10]1([CH3:21])[CH:15]=[CH:14][C:13]([S:16]([NH:19][NH2:20])(=[O:18])=[O:17])=[CH:12][CH:11]=1>CO>[S:16]([NH:19][N:20]=[CH:5][C:4]1[CH:3]=[CH:2][CH:9]=[CH:8][C:6]=1[C:5]1[CH:8]=[CH:9][C:2]([F:1])=[CH:3][CH:4]=1)([C:13]1[CH:12]=[CH:11][C:10]([CH3:21])=[CH:15][CH:14]=1)(=[O:17])=[O:18]

Participants

4

Reactant 2

HCID 15303P-ToluenesulfonylhydrazideHCID 680234-Fluorobenzaldehyde

Product 1

HCID 89760726HCID 89760726, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Fluoro-benzaldehyde (26.6 ml, 31.25 g, 251 mmol) was added all at once to a stirred suspension of 4-tolylsulfonyl hydrazine (43.47 g, 287 mmol) in methanol (200 ml). Within 30 seconds everything dissolved and there was a small exotherm to 32° C., before the temperature dropped. After 30 minutes some of the solvent was evaporated. Crystallisation started after scratching and the solution was left for two hours at room temperature and overnight at ca 5° C. to crystallize. The crystals were filtered off, washed with methanol (2×ca 30 ml), then left in the air to dry, yielding 51.8 g (71%) m.p. 123-125° C.

Workup

  1. dissolutionWithin 30 seconds everything dissolved
  2. customto 32° C.
  3. additionbefore the temperature dropped
  4. customAfter 30 minutes some of the solvent was evaporated
  5. customCrystallisation
  6. customto crystallize
  7. filtrationThe crystals were filtered off
  8. washwashed with methanol (2×ca 30 ml)
  9. waitleft in the air
  10. customto dry
  11. customyielding 51.8 g (71%) m.p. 123-125° C.

Sources & evidence

ORD record
ord-64727c28b02148999121347d29cb4198
Source dataset
uspto-grants-2016_08
Patent number
US09408392B2

Reaction notes

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