Toluene → HCID 57939230, compound

HRID 2091479Notes

Reaction equation

HRID 2091479 reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].C1(C)C=CC=CC=1.[CH2:14]([O:25][C:26]1C=[CH:33][CH:32]=[CH:31][C:27]=1C(O)=O)[CH2:15][CH2:16]/[CH:17]=[CH:18]\[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]>CN(C=O)C.C(Cl)Cl>[CH2:14]([O:25][C:26]1[CH:27]=[CH:31][CH:32]=[CH:33][C:1]=1[C:2]([Cl:4])=[O:3])[CH2:15][CH2:16]/[CH:17]=[CH:18]\[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

6

Reactant 3

HCID 1140TolueneHCID 65578Oxalyl chlorideHCID 57939223HCID 57939223, compound

Product 1

HCID 57939230HCID 57939230, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

800 μL of oxalyl chloride (9.17 mmol) and two drops of anhydrous DMF are added under argon to 76 mg of toluene-dried acid 30 (262 μmol) dissolved in 15 mL of anhydrous DCM. The medium is stirred at room temperature for two hours and then concentrated to give 80 mg of a yellow oil, i.e. a yield of 99%.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-4953439c88ea456e95adde410c1ea303
Source dataset
uspto-grants-2013_05
Patent number
US08440591B2

Reaction notes

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