Thionyl Chloride → HCID 9998156, compound

HRID 1354815Notes

Reaction equation

HRID 1354815 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:15]=[CH:14][C:10]=1[C:11](O)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:28])=O>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:17]=[C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:15]=[CH:14][C:10]=1[C:11]([Cl:28])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 9840634HCID 9840634, compound

Product 1

HCID 9998156HCID 9998156, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

Compound 37 (1 g, 3 mmol) was mixed with thionyl chloride (7.2 g, 60 mmol) and 3 drops of DMF. The reaction mixture was refluxed for 3 h under nitrogen. After cooling down to room temperature, thionyl chloride was removed under reduced pressure. Toluene (5 mL) was then added, and the mixture was dried under reduced pressure again. This process was repeated twice to ensure all the excess of thionyl chloride was removed. The compound 38 was further dried under high vacuum for half an hour and was used directly in the next step without purification.

Workup

  1. temperatureThe reaction mixture was refluxed for 3 h under nitrogen
  2. customthionyl chloride was removed under reduced pressure
  3. additionToluene (5 mL) was then added
  4. customthe mixture was dried under reduced pressure again
  5. customwas removed
  6. dry with materialThe compound 38 was further dried under high vacuum for half an hour
  7. customwas used directly in the next step without purification

Sources & evidence

ORD record
ord-5495d8a47fb143efa8747edd59817654
Source dataset
uspto-grants-2007_05
Patent number
US07223759B2

Reaction notes

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