Toluene → HCID 57939194, compound

HRID 2091475Notes

Reaction equation

HRID 2091475 reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].C1(C)C=CC=CC=1.[CH2:14]([O:25][C:26]1[CH:27]=C([CH:32]=[CH:33][CH:34]=1)C(O)=O)[CH2:15][CH2:16][CH2:17][CH2:18][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]=[C:1]([CH:32]=[CH:33][CH:34]=1)[C:2]([Cl:4])=[O:3])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

6

Reactant 3

HCID 1140TolueneHCID 65578Oxalyl chlorideHCID 57939192HCID 57939192, compound

Product 1

HCID 57939194HCID 57939194, compoundYield 100.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

1 mL of oxalyl chloride (11.5 mmol) and two drops of anhydrous DMF are added under argon to 93 mg of toluene-dried acid 22 (318 μmol) dissolved in 20 mL of anhydrous DCM. The medium is stirred at room temperature for two hours, and then concentrated to give 99 mg of a yellow oil, i.e. a yield of 99%.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-d08653ece4324f4a8f4b92f511b21878
Source dataset
uspto-grants-2013_05
Patent number
US08440591B2

Reaction notes

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