Oxalyl chloride → HCID 59625913, compound

HRID 2365629Notes

Reaction equation

HRID 2365629 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[CH2:5][O:6][C:7]1[CH:15]=[CH:14][C:10]([C:11](O)=[O:12])=[CH:9][C:8]=1[Cl:16].C(Cl)(=O)C([Cl:23])=O>C1COCC1.CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[CH2:5][O:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([Cl:23])=[O:12])=[CH:9][C:8]=1[Cl:16]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 8707028HCID 8707028, compound

Product 1

HCID 59625913HCID 59625913, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of compound 27d (67 mg, 0.33 mmol) in THF (2 mL) was added oxalyl dichloride (43 μL, 0.50 mmol) dropwise at 0° C., followed by the addition of 2 drops of DMF. The resultant mixture was stirred at 0° C. for 3 h, and then was warmed up to room temperature over 18 h. The solvents were removed under reduced pressure. The resultant residue, crude compound 27e, was dried under reduced pressure for 2 h and used in the following step without further purification.

Workup

  1. customThe solvents were removed under reduced pressure
  2. dry with materialThe resultant residue, crude compound 27e, was dried under reduced pressure for 2 h
  3. customused in the following step without further purification

Sources & evidence

ORD record
ord-e7305cd4f4804341a430673871649b5d
Source dataset
uspto-grants-2014_04
Patent number
US08697683B2

Reaction notes

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