Thionyl Chloride → HCID 131722391, compound

HRID 635823Notes

Reaction equation

HRID 635823 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:14](=[CH:15][C:16]=1[O:17][CH3:18])[C@H:13]1[C@H:8]([CH2:9][CH2:10][CH2:11][CH2:12]1)[N:7]=[C:6]2[C:19]1[CH:24]=[CH:23][C:22]([C:25]([OH:27])=[O:26])=[CH:21][CH:20]=1.S(Cl)(Cl)=O.[CH:32]1([CH2:35]O)[CH2:34][CH2:33]1>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:14](=[CH:15][C:16]=1[O:17][CH3:18])[C@H:13]1[C@H:8]([CH2:9][CH2:10][CH2:11][CH2:12]1)[N:7]=[C:6]2[C:19]1[CH:20]=[CH:21][C:22]([C:25]([O:27][CH2:35][CH:32]2[CH2:34][CH2:33]2)=[O:26])=[CH:23][CH:24]=1

Participants

4

Reactant 3

HCID 24386Thionyl ChlorideHCID 75644CyclopropanemethanolHCID 68426637HCID 68426637, compound

Product 1

HCID 131722391HCID 131722391, compound

Conditions

Temperature
50 °C

Procedure

2.0 g of (+/−)-cis-8,9-dimethoxy-6-(4-carboxyphenyl)-1,2,3,4,4a,10b-hexahydrophenanthridine are suspended in 12.0 ml of cyclopropylmethanol, admixed with 1.0 ml of thionyl chloride and stirred at 50° C. for 4 days. The solution is concentrated under reduced pressure and the residue is partitioned between ethyl acetate and dilute sodium bicarbonate solution. The organic phase is dried with sodium sulfate and concentrated. The residue is recrystallized from ethyl acetate. This gives 1.33 g (63.7% of Th.) of the title compound of m.p.: 147-148° C.

Workup

  1. concentrationThe solution is concentrated under reduced pressure
  2. customthe residue is partitioned between ethyl acetate and dilute sodium bicarbonate solution
  3. dry with materialThe organic phase is dried with sodium sulfate
  4. concentrationconcentrated
  5. customThe residue is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-9ceb208886db41cfbbeea6f2b99a15ce
Source dataset
uspto-grants-2001_02
Patent number
US06191138B1

Reaction notes

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