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Oxalyl chloride → HCID 86615543, compound

HRID 883940
Notes
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Reaction equation

HRID 883940 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 65578Oxalyl chlorideHCID 67040084HCID 67040084, compound

Product 1

HCID 86615543HCID 86615543, compoundYield 110.2%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent
HCID 8028
Tetrahydrofuran
Solvent

Procedure

A suspension of the product of Example 52B (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-ec50b286f54640728c91c9427a842340
Source dataset
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08236950B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes