Oxalyl chloride → HCID 72342783, compound

HRID 2365640Notes

Reaction equation

HRID 2365640 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH:12]1[CH2:16][CH2:15][N:14]([C:17]([N:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)=[O:18])[CH2:13]1)[C:5](O)=[O:6].C(Cl)(=O)C([Cl:27])=O>C1COCC1.CN(C=O)C>[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH:12]1[CH2:16][CH2:15][N:14]([C:17]([N:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)=[O:18])[CH2:13]1)[C:5]([Cl:27])=[O:6]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 66770198HCID 66770198, compound

Product 1

HCID 72342783HCID 72342783, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of compound 34e (166 mg, 0.39 mmol) in THF (4 mL) was added oxalyl dichloride (43 μL, 0.50 mmol) dropwise at 0° C., followed by the addition of 2 drops of DMF. The resulting mixture was stirred at 0° C. for 3 h, warmed to room temperature, and stirred for 18 h. The solvents were removed under reduced pressure. The resultant residue, compound 34f, was dried under reduced pressure for 2 h and used in the following step without further purification.

Workup

  1. temperaturewarmed to room temperature
  2. stirringstirred for 18 h
  3. customThe solvents were removed under reduced pressure
  4. dry with materialThe resultant residue, compound 34f, was dried under reduced pressure for 2 h
  5. customused in the following step without further purification

Sources & evidence

ORD record
ord-adeb3818cc38421ebd26188d2114efe8
Source dataset
uspto-grants-2014_04
Patent number
US08697683B2

Reaction notes

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