Sodium Chloride → N-Ethenyl-N-hexylformamide

HRID 720810Notes

Reaction equation

[CH2:1]([N:5]([CH:8]=[CH2:9])[CH:6]=[O:7])[CH2:2][CH2:3][CH3:4].Br[CH2:11][CH2:12]CCCC.[Na+].[Cl-]>>[CH2:1]([N:5]([CH:8]=[CH2:9])[CH:6]=[O:7])[CH2:2][CH2:3][CH2:4][CH2:11][CH3:12]

Participants

Reactant 3

HCID 5234Sodium Chloride

HCID 81011-Bromohexane

HCID 15812116N-Butyl-N-ethenylformamide

Product 1

HCID 21895372N-Ethenyl-N-hexylformamideYield 63%

Procedure

The synthetic procedure was identical to that described for the preparation of 1a, where 1-bromohexane is used in place of 1-bromobutane. Yield: 63%; IR (NaCl, v: cm−1): 1698 (—NHC(═O)H); 1630 (C═C); 1H-NMR (CDCl3, δ: ppm): 8.31, 8.14 (2s, 1H, —C(═O)H); 7.25–7.16, 6.61–6.52 (m, 1H, H2C═CH—); 4.65–4.54 (m, 1H, HaHbC═CH—); 4.45–4.42 (s, 1H, HaHbC═CH—); 3.60–3.44 (t, 2H, —NCH2CH2—); 1.65–1.56 (m, 2H, —CH2CH2CH2—); 1.31 (m, 6H, —CH2(CH2)3CH3); 0.90–0.88 (t, 3H, —NCH2CH2(CH2)3CH3).

Sources & evidence

ORD record: ord-9365cfd7ebe949f79b94aee7b1b4c764
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07135598B2

Reaction notes

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