HCID 14323749, compound → HCID 20085749, compound

HRID 1742465Notes

Reaction equation

HRID 1742465 reaction equation
[CH3:1][C:2]1([CH3:17])[CH2:7][CH:6]([NH:8][C:9](=[O:14])[C:10]([O:12]C)=O)[CH2:5][C:4]([CH3:16])([CH3:15])[NH:3]1.[C:18]([C:22]1[CH:23]=[C:24]([NH:33][C:34]([C:36]([NH:38][NH2:39])=[O:37])=[O:35])[CH:25]=[C:26]([C:29]([CH3:32])([CH3:31])[CH3:30])[C:27]=1[OH:28])([CH3:21])([CH3:20])[CH3:19]>CO>[CH3:17][C:2]1([CH3:1])[CH2:7][CH:6]([NH:8][C:9](=[O:14])[C:10]([NH:39][NH:38][C:36](=[O:37])[C:34]([NH:33][C:24]2[CH:25]=[C:26]([C:29]([CH3:31])([CH3:32])[CH3:30])[C:27]([OH:28])=[C:22]([C:18]([CH3:21])([CH3:20])[CH3:19])[CH:23]=2)=[O:35])=[O:12])[CH2:5][C:4]([CH3:16])([CH3:15])[NH:3]1

Participants

4

Reactant 2

HCID 14323749HCID 14323749, compoundHCID 23369036HCID 23369036, compound

Product 1

HCID 20085749HCID 20085749, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Conditions

Temperature
15 °C

Procedure

Into a 3-necked 300 ml flask was introduced a 58% solution of methyl N-(2,2,6,6-tetramethyl-4-piperidinyl)oxamate in methanol (8.3 g, 0.02 mole), N-(3,5-di-t-butyl-4-hydroxyphenyl)-N'-aminooxamide (6.1 g, 0.02 mole) and 100 ml of anhydrous methanol. The flask was equipped with a magnetic stirrer, a thermometer and a Dean Stark trap containing a reflux condenser. The reaction mixture was heated in an oil bath to reflux for 31/2 hours. At this point, the Dean Stark trap was periodically drained until 40 ml of methanol was collected and solid material formed in the reaction mixture. An additional 10 ml of methanol was distilled from the reaction mixture. The reaction mixture was cooled to 15° C. and the resulting thick slurry was filtered. The filter cake was rinsed with 20 ml of cold methanol and air dried. The product was a white solid weighing 6.2 grams and had a melting range of 196°-202° C. The infrared scan (nujol mull) contained sharp carbonyl bands at 1665, 1585 and 1510 cm-1.

Workup

  1. customThe flask was equipped with a magnetic stirrer
  2. additiona thermometer and a Dean Stark trap containing a reflux condenser
  3. temperatureThe reaction mixture was heated in an oil bath
  4. temperatureto reflux for 31/2 hours
  5. customwas collected
  6. customsolid material formed in the reaction mixture
  7. distillationAn additional 10 ml of methanol was distilled from the reaction mixture
  8. filtrationthe resulting thick slurry was filtered
  9. washThe filter cake was rinsed with 20 ml of cold methanol and air
  10. customdried

Sources & evidence

ORD record
ord-422bd40a67ae4b5aabd890be5f2034a4
Source dataset
uspto-grants-1994_08
Patent number
US05338853

Reaction notes

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