Tert-Butylamine → N-tert-butylisobutyramide

HRID 1855614Notes

Reaction equation

[C:1]([NH:5][C:6](=[O:11])[C:7](C)([CH3:9])[CH3:8])([CH3:4])([CH3:3])[CH3:2].C(N)(C)(C)C.C(N(CC)CC)C.C(Cl)(=O)C(C)C>>[C:1]([NH:5][C:6](=[O:11])[CH:7]([CH3:9])[CH3:8])([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 4

HCID 6385Tert-Butylamine

HCID 8471Triethylamine

HCID 62325Isobutyryl chloride

HCID 299326N-tert-Butylpivalamide

Product 1

HCID 344892N-tert-butylisobutyramideYield 96%

Procedure

In a fashion similar to the preparation of LtBu,tBuH, treatment of tert-butylamine (11.3 mL, 105 mmol) and triethylamine (14.9 mL, 105 mmol) with isobutyryl chloride (10.8 mL, 100 mmol) afforded LiPr,tBuH as white crystalline solid (13.75 g, 96%) upon sublimation at 55° C./0.05 Torr: mp 117-119° C.

Sources & evidence

ORD record: ord-3ae2ff0ca1264e9284ebdc3f6d5e9051
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962876B2

Reaction notes

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