Dimethylformamide → HCID 12349168, compound

HRID 514419Notes

Reaction equation

HRID 514419 reaction equation
CN(C)C(OC(C)(C)C)N(C)C.[C:13]([O:17][CH2:18][CH3:19])(=[O:16])[CH2:14][CH3:15].[CH3:20][N:21]([CH:23]=O)[CH3:22]>>[CH3:22][N:21]([CH3:20])/[CH:23]=[C:14](\[CH3:15])/[C:13]([O:17][CH2:18][CH3:19])=[O:16]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 7749Ethyl PropionateHCID 79885tert-Butoxy bis(dimethylamino)methane

Product 1

HCID 12349168HCID 12349168, compoundYield 30%

Procedure

A solution of N,N,N′,N′-tetramethyl-1-[(2-methylpropan-2-yl)oxy]methanediamine (2.47 g, 14.19 mmol), ethyl propionate (2.17 g, 21.27 mmol) and DMF (2 mL) in a sealed tube was heated to 90° C. for 24 h. Then extracted with ethyl acetate, collected the organic phase and washed with water, brine and dried with anhydrous sodium sulfate. Organic phase was concentrated and purified by silica gel chromatograph to give 0.68 g of the title compound (30%). 1H NMR (400 MHz, CDCl3): δ 1.24 (3H, t, J=7.2 Hz), 1.95 (3H, s), 3.00 (6H, s), 4.11 (2H, q, J=7.2 Hz), 7.28 (1H, s). [M+H] Calc'd for C8H15NO2, 158. Found, 158.

Workup

  1. extractionThen extracted with ethyl acetate
  2. customcollected the organic phase
  3. washwashed with water, brine
  4. dry with materialdried with anhydrous sodium sulfate
  5. concentrationOrganic phase was concentrated
  6. custompurified by silica gel chromatograph

Sources & evidence

ORD record
ord-597ccefe891b48469860d7749e41730b
Source dataset
uspto-grants-2015_08
Patent number
US09107916B2

Reaction notes

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