1,2-Dichloroethane → N-methoxy-N-methylhept-6-enamide

HRID 1879244Notes

Reaction equation

HRID 1879244 reaction equation
C(Cl)CCl.[C:5]([OH:13])(=O)[CH2:6][CH2:7][CH2:8][CH2:9][CH:10]=[CH2:11].[Cl-].[CH3:15][O:16][NH2+:17][CH3:18]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:15][O:16][N:17]([CH3:18])[C:5](=[O:13])[CH2:6][CH2:7][CH2:8][CH2:9][CH:10]=[CH2:11]

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 707056-Heptenoic acidHCID 11040634Methoxy(methyl)azanium;chloride

Product 1

HCID 46703846N-methoxy-N-methylhept-6-enamideYield 97%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

EDC (1.1 eq.) was added in small portions over 1.5 h to a stirred mixture of hept-6-enoic acid, methoxy(methyl)ammonium chloride (1.1 eq.) and DMAP (1.1 eq.) in CH2Cl2 (0.2 M). After 14 h, the mixture was diluted with CH2Cl2, then washed sequentially with hydrochloric acid (1 M), NaOH (1M), brine and dried (Na2SO4). Evaporation of the solvent afforded the title compound (97%) as a colorless oil. 1H NMR (400 MHz, CDCl3, 300 K) δ 5.87-5.75 (m, 1H), 5.01 (d, J 17.1, 1H), 4.95 (d, J 10.1, 1H), 3.68 (s, 3H), 3.18 (s, 3H), 2.48-2.36 (m, 2H), 2.13-2.04 (m, 2H), 1.71-1.60 (m, 2H), 1.50-1.40 (m, 2H).

Workup

  1. washwashed sequentially with hydrochloric acid (1 M), NaOH (1M), brine
  2. dry with materialdried (Na2SO4)
  3. customEvaporation of the solvent

Sources & evidence

ORD record
ord-3793365b54694eabbd614a7081c47ada
Source dataset
uspto-grants-2012_11
Patent number
US08314062B2

Reaction notes

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