Hydrochloric Acid → HCID 58800192, compound

HRID 347289Notes

Reaction equation

HRID 347289 reaction equation
[CH2:1]([O:13][C:14]1[CH:20]=[CH:19][C:17]([NH2:18])=[CH:16][CH:15]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].N1C=CC=CC=1.Cl[C:28](=[O:34])[C:29]([O:31][CH2:32][CH3:33])=[O:30].Cl>C(Cl)Cl>[CH2:32]([O:31][C:29](=[O:30])[C:28]([NH:18][C:17]1[CH:19]=[CH:20][C:14]([O:13][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[CH:15][CH:16]=1)=[O:34])[CH3:33]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 20884Ethoxalyl chlorideHCID 34986334-n-dodecyloxyaniline

Product 1

HCID 58800192HCID 58800192, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

In a 1 L jacketed flask under a nitrogen atmosphere is added 60 g (0.2425 mols) of p-dodecyloxyaniline, 650 mL of CH2Cl2 and 56.6 g of pyridine (0.716 mols) and the resulting solution is cooled to 0° C. Maintaining an internal temperature below 5° C., 46.3 g (0.339 mols) of ethyl chlorooxoacetate is then added dropwise over a period of one hour. After the addition is complete, the internal temperature is maintained at 10° C. overnight. To the resultant reaction mixture is added rapidly 400 mL of 1N HCl and the resultant mixture is allowed to warm to RT. The reaction mixture is stirred for one hour than the organic phase separated. The organic phase is dried over anhydrous sodium sulphate and isolubles removed by filtration. The volatiles are removed in vacuo and the residue is recrystallized from ethanol (250 mL). The solid is washed twice with ethanol (50 mL) at 0° C. to give 64.1 g of a white solid, mp. 70.5–72° C. The NMR, MS and IR spectra are consistent with the product.

Workup

  1. additionis then added dropwise over a period of one hour
  2. additionAfter the addition
  3. temperaturethe internal temperature is maintained at 10° C. overnight
  4. customTo the resultant reaction mixture
  5. temperatureto warm to RT
  6. customseparated
  7. dry with materialThe organic phase is dried over anhydrous sodium sulphate
  8. customisolubles removed by filtration
  9. customThe volatiles are removed in vacuo
  10. customthe residue is recrystallized from ethanol (250 mL)
  11. washThe solid is washed twice with ethanol (50 mL) at 0° C.

Sources & evidence

ORD record
ord-76024f4c5d4247f686090fb17a841cb1
Source dataset
uspto-grants-2007_02
Patent number
US07173128B2

Reaction notes

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