Tert-Butylamine → HCID 60710552, compound

HRID 624898Notes

Reaction equation

HRID 624898 reaction equation
[CH3:1][C:2]([NH2:5])([CH3:4])[CH3:3].Cl[CH2:7][C:8]1[O:9][C:10]([CH3:13])=[N:11][N:12]=1>CN(C=O)C>[CH3:1][C:2]([NH:5][CH2:7][C:8]1[O:9][C:10]([CH3:13])=[N:11][N:12]=1)([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 38266202-(Chloromethyl)-5-methyl-1,3,4-oxadiazole

Product 1

HCID 60710552HCID 60710552, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 2-methylpropan-2-amine (75-64-9, 141 mg, 202 μL, 1.92 mmol) and 2-(chloromethyl)-5-methyl-1,3,4-oxadiazole (3914-42-9, 50 mg, 377 μmol) in DMF (200 μL) was stirred at ambient temperature for 16 h. The mixture was poured onto ice-water (20 mL) and extracted with CH2Cl2 (2×30 mL). The combined extracts were washed with ice-water (20 mL), dried over Na2SO4 and concentrated in vacuo to give a yellow oil. The crude product was purified by preparative TLC (silica gel 1 mm, EtOAc/diethyl amine 95:5, elution with DCM/EtOAc 1:1) to give the title compound (45 mg, 71%) as yellow oil; MS (EI): m/e=170.2 [MH+].

Workup

  1. additionThe mixture was poured onto ice-water (20 mL)
  2. extractionextracted with CH2Cl2 (2×30 mL)
  3. washThe combined extracts were washed with ice-water (20 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customto give a yellow oil
  7. customThe crude product was purified by preparative TLC (silica gel 1 mm, EtOAc/diethyl amine 95:5, elution with DCM/EtOAc 1:1)

Sources & evidence

ORD record
ord-e34612b8f8f44030b2167e08628cf4d2
Source dataset
uspto-grants-2016_04
Patent number
US09303012B2

Reaction notes

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