1,2-Dichloroethane → 11,14-Eicosadienamide

HRID 76330Notes

Reaction equation

HRID 76330 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.

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-5f07ed7365ce4b8c835b7f3890a5b4b6
Source dataset
uspto-grants-2014_09
Patent number
US08835623B2

Reaction notes

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