Thionyl Chloride → HCID 13427181, compound

HRID 2372363Notes

Reaction equation

HRID 2372363 reaction equation
C([N:3](C([O-])=O)[N:4]=[C:5]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][C:16]=1[O:23][CH3:24])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1)C.O=[S:29](Cl)Cl>>[CH3:24][O:23][C:16]1[CH:17]=[C:18]([O:21][CH3:22])[CH:19]=[CH:20][C:15]=1[C:5]1[N:4]=[N:3][S:29][C:6]=1[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 131717208HCID 131717208, compound

Product 1

HCID 13427181HCID 13427181, compoundYield 44.7%

Procedure

Acylhydrazone 15 (4.32 g, 11.6 mmol) was added to SOCl2 (50 ml) at 0° C. The reaction was allowed to warm to room temperature. The reaction was complete (by TLC) after 3 hours. SOCl2 was removed under reduced pressure and the crude brown oil was chromatographed on 350 g SIO2, eluting with 4:1, CH2Cl2 :Hexane to afford 13 (1.7 g, 44.7%), m.p. 90-91.5.

Workup

  1. customafter 3 hours
  2. customSOCl2 was removed under reduced pressure
  3. customthe crude brown oil was chromatographed on 350 g SIO2
  4. washeluting with 4:1, CH2Cl2

Sources & evidence

ORD record
ord-690f5756204943ccb197443cf2ae80a4
Source dataset
uspto-grants-1992_03
Patent number
US05098918

Reaction notes

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