Sodium Chloride → N-Cyclopropyl-3Z-hexenamide

HRID 2054724Notes

Reaction equation

HRID 2054724 reaction equation
[C:1]([OH:8])(=O)/[CH:2]=[CH:3]\[CH2:4][CH2:5][CH3:6].ClC(OCC)=O.C(N(CC)CC)C.[CH:22]1([NH2:25])[CH2:24][CH2:23]1.[Cl-].[Na+]>C1COCC1>[CH:22]1([NH:25][C:1](=[O:8])/[CH:2]=[CH:3]\[CH2:4][CH2:5][CH3:6])[CH2:24][CH2:23]1

Participants

7

Reactant 5

HCID 5234Sodium ChlorideHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 69828CyclopropylamineHCID 12467038(Z)-Hex-2-enoic acid

Product 1

HCID 86597466N-Cyclopropyl-3Z-hexenamideYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3Z-Hexenoic acid 1 eq, ethyl chloroformate 1.1 eq, triethylamine 1.2 eq, cyclopropylamine 1.5 eq as a 2.0M solution in THF, quench with 10% sodium chloride solution, yield=77%. 0.49 ppm (m, 2H), 0.75 ppm (m, 2H), 0.98 ppm (t, 3H, J=7.48 Hz), 2.05 ppm (d, 2H, J=0.97 Hz, of pentet, J=7.46 Hz), 2.70 ppm (octet, 1H, J=3.59 Hz), 2.98 ppm (d, 2H, J=7.46 Hz), 5.46-5.52 ppm (m, 1H), 5.58-5.66 ppm (m, 1H), 6.19 ppm (br. s, 1H).

Sources & evidence

ORD record
ord-1aeaf511734d4463973ce90d98b9830e
Source dataset
uspto-grants-2008_02
Patent number
US07329767B2

Reaction notes

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