Tert-Butylamine → N-tert-Butylpivalamide

HRID 1855613Notes

Reaction equation

HRID 1855613 reaction equation
[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:13](Cl)(=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15]>C(OCC)C>[C:1]([NH:5][C:13](=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6385Tert-ButylamineHCID 8471TriethylamineHCID 62493Pivaloyl chloride

Product 1

HCID 299326N-tert-ButylpivalamideYield 98%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A 1 L three-necked round-bottomed flask was charged with diethylether (500 mL), tert-butylamine (11.3 mL, 105 mmol), and triethylamine (14.9 mL, 105 mmol). To this vigorously stirred solution at 0° C. was slowly added pivaloyl chloride (8.9 mL, 100 mmol) and the resultant white slurry was stirred for 18 h at ambient temperature. This slurry was then filtered with a water aspirator pump and the volatile components of the filtrate were removed under reduced pressure. The resultant crystalline solid was sublimed at 55° C./0.05 Torr to afford LtBu,tBuH as white crystals (15.41 g, 98%): mp 116-118° C.

Workup

  1. customat 0° C.
  2. filtrationThis slurry was then filtered with a water aspirator pump
  3. customthe volatile components of the filtrate were removed under reduced pressure
  4. customwas sublimed at 55° C.

Sources & evidence

ORD record
ord-62066e006b3342f3be1c7538df6ded3e
Source dataset
uspto-grants-2015_02
Patent number
US08962876B2

Reaction notes

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