Thionyl Chloride → HCID 13427185, compound

HRID 2372368Notes

Reaction equation

HRID 2372368 reaction equation
C([N:3](C([O-])=O)[N:4]=[C:5]([C:12]1[S:13][CH:14]=[CH:15][CH:16]=1)[CH2:6][C:7]1[S:8][CH:9]=[CH:10][CH:11]=1)C.O=[S:21](Cl)Cl>>[S:13]1[CH:14]=[CH:15][CH:16]=[C:12]1[C:5]1[N:4]=[N:3][S:21][C:6]=1[C:7]1[S:8][CH:9]=[CH:10][CH:11]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 86745572HCID 86745572, compound

Product 1

HCID 13427185HCID 13427185, compoundYield 66%

Procedure

Acylhydrazine 31 (14.13 g, 14.04 mmol) was added to SOCl2 (60 ml) at 0° C. The reaction was allowed to warm to room temperature. The reaction was complete (by TLC) after 2 hours. SOCl2 was removed under reduced pressure. The dark residue was chromatographed on SiO2 (300 g), eluting with CH2Cl2. The isolated oil was bulb to bulb distilled at 0.2 mm (Hg) at 150° C. to yield 29 (2.3 g, 66.0%).

Workup

  1. customafter 2 hours
  2. customSOCl2 was removed under reduced pressure
  3. customThe dark residue was chromatographed on SiO2 (300 g)
  4. washeluting with CH2Cl2
  5. distillationdistilled at 0.2 mm (Hg) at 150° C.

Sources & evidence

ORD record
ord-a43ce8bdf90c4b82b2910d9adae4cf61
Source dataset
uspto-grants-1992_03
Patent number
US05098918

Reaction notes

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