Oxalyl chloride → HCID 178521130, compound

HRID 1611400Notes

Reaction equation

HRID 1611400 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][C:11]([C:13](O)=[O:14])=[N:10][C:9]=2[C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)=[CH:4][C:3]=1[OH:22].C(Cl)(=O)C([Cl:26])=O>ClCCl.CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][C:11]([C:13]([Cl:26])=[O:14])=[N:10][C:9]=2[C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)=[CH:4][C:3]=1[OH:22]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 178524861HCID 178524861, compound

Product 1

HCID 178521130HCID 178521130, compoundYield 119.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

A suspension of the product from Step 1 (1.24 g, 3.9 mmol) in dichloromethane (50 ml) was treated with oxalyl chloride (3.4 ml, 39 mmol) and 10 drops dimethylformamide. The suspension was then heated at reflux for 5 hours, cooled and concentrated under vacuum. The resultant residue was azeotroped with toluene then trituated with hexane to afford the title compound (1.56 g), which was used without further purification.

Workup

  1. temperatureThe suspension was then heated
  2. temperatureat reflux for 5 hours
  3. temperaturecooled
  4. concentrationconcentrated under vacuum
  5. customThe resultant residue was azeotroped with toluene

Sources & evidence

ORD record
ord-f3a27ab50f46401685807e2ed93a8269
Source dataset
uspto-grants-2006_01
Patent number
US06987119B2

Reaction notes

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