Oxalyl chloride → HCID 86615543, compound

HRID 605066Notes

Reaction equation

HRID 605066 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([S:25][C:26]4[CH:34]=[CH:33][C:29]([C:30](O)=[O:31])=[CH:28][C:27]=4[N+:35]([O-:37])=[O:36])=[CH:21][CH:20]=3)=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)C([Cl:41])=O>C(Cl)Cl.O1CCCC1.CN(C)C=O>[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16](=[O:17])[NH:18][C:19]3[CH:24]=[CH:23][C:22]([S:25][C:26]4[CH:34]=[CH:33][C:29]([C:30]([Cl:41])=[O:31])=[CH:28][C:27]=4[N+:35]([O-:37])=[O:36])=[CH:21][CH:20]=3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 2

HCID 65578Oxalyl chlorideHCID 67040084HCID 67040084, compound

Product 1

HCID 86615543HCID 86615543, compoundYield 110.2%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of the product of Example 19B (500 mg, 0.976 mmol) in anhydrous methylene chloride (10 mL) and tetrahydrofuran (5 mL) was treated with oxalyl chloride (2M in methylene chloride, 0.976 mL, 1.951 mmol) and N,N-dimethylformamide (3 drops), and the resulting solution was stirred under a nitrogen atmosphere for 2 hours at room temperature. The solvent was removed by rotary evaporation in vacuo and the residue dried on hi-vacuum to give the title compound as a yellow solid (0.571 g).

Workup

  1. customThe solvent was removed by rotary evaporation in vacuo
  2. customthe residue dried on hi-vacuum

Sources & evidence

ORD record
ord-4bd4d73dc22a4440a4a9668d2c771783
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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