Formamide → 5-tert-butyl-1H-imidazole

HRID 7106

Reaction equation

Br[CH2:2][C:3](=O)[C:4]([CH3:7])([CH3:6])[CH3:5].[CH:9]([NH2:11])=O.C(Cl)Cl.CO.[NH4+:17].[OH-]>>[C:4]([C:3]1[NH:11][CH:9]=[N:17][CH:2]=1)([CH3:7])([CH3:6])[CH3:5]

Participants

Reactant 3

HCID 713Formamide

HCID 21642Bromopinacolone

HCID 21896990Dichloromethane methanol ammonium hydroxide

Product 1

HCID 4984365-tert-butyl-1H-imidazoleYield 21%

Procedure

Reaction of 1-bromo-3,3-dimethyl-butan-2-one (3.0 g, 16.80 mmol), and formamide (4.7 mL, 117.20 mmol), followed by chromatography (CH2Cl2/MeOH/NH4OH 94:3:3) gave the title compound (450 mg, 21%) as a yellow foam. 1H NMR (300 MHz, CDCl3) δ 1.29 (s, 9H), 6.77 (s, 1H), 7.57, (s, 1H). ES-MS m/z 125 (M+H).

Sources & evidence

ORD record: ord-387a8ed2067c4b49ae065cb773dcae43
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07084155B2

Linked notes

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