Thionyl Chloride → HCID 69662020, compound

HRID 892113Notes

Reaction equation

HRID 892113 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[N:12][C:13]([Cl:28])=[N:14][C:15]=2[NH:17][C@H:18]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:19]O)[N:10]=[C:9]1[CH:29]1[CH2:33][CH2:32][CH2:31][CH2:30]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)(Cl)=O>>[CH2:1]([N:8]1[C:16]2[C:15]3=[N:17][C@H:18]([CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH2:19][N:14]3[C:13]([Cl:28])=[N:12][C:11]=2[N:10]=[C:9]1[CH:29]1[CH2:33][CH2:32][CH2:31][CH2:30]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 86589632HCID 86589632, compound

Product 1

HCID 69662020HCID 69662020, compoundYield 104%

Conditions

Temperature
60 °C

Procedure

To Compound C2 (1.87 g, 4.05 mmol) obtained in Reference Example 37 was added thionyl chloride (15.0 mL, 207 mmol, 51 equivalents) and the mixture was stirred with heating at 60° C. for 1 hour. The reaction solution was concentrated under reduced pressure, the solvent was azeotroped with toluene, to the residue were carefully added chloroform and saturated sodium hydrogen carbonate, and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was extracted with chloroform, then the organic layer was washed with saturated aqueous sodium chloride and dried over anhydrous sodium sulfate, and the solvent was evaporated. The residue was purified by silica gel column chromatography (chloroform:methanol=90:10) to obtain the title compound (1.87 g, 99%).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customthe solvent was azeotroped with toluene, to the residue
  3. stirringthe mixture was stirred at room temperature for 30 minutes
  4. extractionThe reaction mixture was extracted with chloroform
  5. washthe organic layer was washed with saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was evaporated
  8. customThe residue was purified by silica gel column chromatography (chloroform:methanol=90:10)

Sources & evidence

ORD record
ord-492a48f331e245129301049577298dc5
Source dataset
uspto-grants-2006_02
Patent number
US07005430B2

Reaction notes

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