1,2-Dichloroethane → 11,14-Eicosadienamide

HRID 573493Notes

Reaction equation

HRID 573493 reaction equation
[C:1]([OH:22])(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]=[CH:12][CH2:13][CH:14]=[CH:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].Cl.C[NH:25]OC.C1C=NC2N(O)N=NC=2C=1.CCN(CC)CC.C(Cl)CCl>C(Cl)Cl>[C:1]([NH2:25])(=[O:22])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]=[CH:12][CH2:13][CH:14]=[CH:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 320811,14-Eicosadienoic acidHCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 181649HOAt

Product 1

HCID 5410154411,14-EicosadienamideYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

11,14-Eicosadienoic acid, (11Z,14Z)- (50 g, 162 mmol), N,O-Dimethylhydroxylamine hydrochloride (31.6 g, 324 mmol), HOAt (44.1 g, 324 mmol), Et3N (45.2 mL, 324 mmol), and EDC (62.1 g, 324 mmol) were mixed in DCM (810 mL) and stirred overnight at ambient temperature. Reaction was then washed 5×700 mL water, then washed 1×600 mL 1 M NaOH, dried with sodium sulfate, filtered through celite and evaporated to obtain 53.06 g (93%) 11,14-eicosadienamide, N-methoxy-N-methyl-, (11Z,14Z) as a clear golden oil. 1H NMR (400 MHz, CDCl3) δ 5.35 (m, 4H), 3.68 (s, 3H), 3.18 (s, 3H), 2.77 (m, 2H), 2.41 (t, J=7 Hz, 2H), 2.05 (m, 4H), 1.63 (m, 2H), 1.40-1.26 (m, 18H), 0.89 (t, J=7 Hz, 3H).

Workup

  1. customReaction
  2. washwas then washed 5×700 mL water
  3. washwashed 1×600 mL 1 M NaOH
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered through celite
  6. customevaporated

Sources & evidence

ORD record
ord-fb334f28c1654223a01ac5ba3d6536ee
Source dataset
uspto-grants-2015_05
Patent number
US09029590B2

Reaction notes

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