Thionyl Chloride → HCID 13427179, compound

HRID 2372362Notes

Reaction equation

HRID 2372362 reaction equation
C([N:3](C([O-])=O)[N:4]=[C:5]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1)[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)C.O=[S:25](Cl)Cl>>[CH3:20][O:19][C:16]1[CH:17]=[CH:18][C:13]([C:5]2[N:4]=[N:3][S:25][C:6]=2[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[CH:14][CH:15]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 86745571HCID 86745571, compound

Product 1

HCID 13427179HCID 13427179, compoundYield 64.6%

Conditions

Temperature
60 °C

Procedure

The acylhydrazine 12 (23.4 g, 75.0 mmol) was added to SOCl2 (200 ml) at 0° C. The reaction was warmed to 60° C. and complete (by TLC) after 3 hours. SOCl2 was removed under reduced pressure. The solid residue was dissolved in EtOAc, washed once with 10% aqueous NaOH and brine. The organic layer was dried over MgSO4, and the solvent was removed under reduced pressure. The crude solid was recrystallized from Et2O to afford 10 (13.0 g, 64.6%), m.p. 81.5°-82.5° C.

Workup

  1. customSOCl2 was removed under reduced pressure
  2. dissolutionThe solid residue was dissolved in EtOAc
  3. washwashed once with 10% aqueous NaOH and brine
  4. dry with materialThe organic layer was dried over MgSO4
  5. customthe solvent was removed under reduced pressure
  6. customThe crude solid was recrystallized from Et2O

Sources & evidence

ORD record
ord-caa88408979042468005e89be8f58138
Source dataset
uspto-grants-1992_03
Patent number
US05098918

Reaction notes

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