Triethylamine → HCID 67372739, compound

HRID 1676889Notes

Reaction equation

HRID 1676889 reaction equation
[C:1](Cl)(=[O:5])[C:2](Cl)=[O:3].[C:7]([C:11]1[CH:12]=[C:13]([CH:15]=[C:16]([C:18]([CH3:21])([CH3:20])[CH3:19])[CH:17]=1)[NH2:14])([CH3:10])([CH3:9])[CH3:8].C([N:24]([CH2:27][CH3:28])CC)C>C1COCC1>[C:18]([C:16]1[CH:15]=[C:13]([NH:14][C:2]([C:1]([NH:24][C:27]2[CH:28]=[C:16]([C:18]([CH3:20])([CH3:19])[CH3:21])[CH:17]=[C:11]([C:7]([CH3:10])([CH3:9])[CH3:8])[CH:12]=2)=[O:5])=[O:3])[CH:12]=[C:11]([C:7]([CH3:10])([CH3:9])[CH3:8])[CH:17]=1)([CH3:21])([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 754193,5-Di-tert-butylaniline

Product 1

HCID 67372739HCID 67372739, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Oxalyl chloride (2.16 mL, 25 mmol) was added dropwise to a stirred solution of 3,5-di-t-butylaniline (10.28 g, 50 mmol) and triethylamine (7.0 mL, 50 mmol) in THF (200 mL) at 0° C. Upon addition, the reaction was allowed to warm up to r.t. and stirred for 1 h. The reaction mixture was then concentrated in vacuo and diluted with water (100 mL). The white precipitate was collected by filtration, washed with dilute HCl (100 mL), water (2×100 mL), and dried in vacuo. Obtained 9.07 g (78%) of N,N′-Bis(3,5-di-t-butylphenyl)oxamide as a white solid.

Workup

  1. additionUpon addition
  2. concentrationThe reaction mixture was then concentrated in vacuo
  3. additiondiluted with water (100 mL)
  4. filtrationThe white precipitate was collected by filtration
  5. washwashed with dilute HCl (100 mL), water (2×100 mL)
  6. customdried in vacuo

Sources & evidence

ORD record
ord-6175812f9d9247dd81a888dc66f29695
Source dataset
uspto-grants-2011_08
Patent number
US08008224B2

Reaction notes

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