tert-Butanol → HCID 178457539, compound

HRID 525908Notes

Reaction equation

HRID 525908 reaction equation
[C:1](=[N:6][CH:7]([CH3:9])[CH3:8])=[N:2][CH:3]([CH3:5])[CH3:4].[CH3:10][C:11]([OH:14])([CH3:13])[CH3:12]>[Cu]Cl>[CH:3]([NH:2]/[C:1](=[N:6]\[CH:7]([CH3:9])[CH3:8])/[O:14][C:11]([CH3:13])([CH3:12])[CH3:10])([CH3:5])[CH3:4]

Participants

4

Reactant 2

HCID 6386tert-ButanolHCID 12734Diisopropylcarbodiimide

Product 1

HCID 178457539HCID 178457539, compoundYield 70.3%

Reagents, catalysts & solvents 1

HCID 62652Cuprous chlorideCatalyst

Procedure

To a solution of N,N′-methanediylidenebis(propan-2-amine) (307 ml, 1981 mmol) in t-BuOH (227 ml, 2377 mmol) at r.t. was added copper(I) chloride (1.961 g, 19.81 mmol). The reaction was stirred at room temperature for 24 h and the resulting mixture was distilled under reduced pressure to afford (E)-tert-butyl N,N′-diisopropylcarbamimidate (279 g, 1393 mmol, 70.3% yield) as a colorless liquid. 1H NMR (400 MHz, CHLOROFORM-d4) δ ppm 1.04 (d, J=−6.06 Hz, 6 H) 1.08 (d, J=6.57 Hz, 6 H) 1.46 (s, 9 H) 2.98-3.19 (m, 1 H) 3.25 (m, 1 H) 3.64 (s, 1 H)

Workup

  1. distillationthe resulting mixture was distilled under reduced pressure

Sources & evidence

ORD record
ord-fea309f4f4f6408aad2a88c13f64254f
Source dataset
uspto-grants-2016_05
Patent number
US09340556B2

Reaction notes

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