Diethyl Ether → HCID 58288630, compound

HRID 335064Notes

Reaction equation

HRID 335064 reaction equation
[C:1](Cl)(=[O:4])[CH:2]=[CH2:3].[CH3:6][O:7][NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][NH:15][O:16][CH3:17].[C:18]([O-:21])([O-])=O.[Na+].[Na+].[CH2:24](OCC)[CH3:25]>>[C:1]([N:15]([CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][N:8]([O:7][CH3:6])[C:18](=[O:21])[CH:24]=[CH2:25])[O:16][CH3:17])(=[O:4])[CH:2]=[CH2:3]

Participants

5

Reactant 4

HCID 3283Diethyl EtherHCID 10340Sodium CarbonateHCID 13140Acryloyl chlorideHCID 58288617HCID 58288617, compound

Product 1

HCID 58288630HCID 58288630, compoundYield 79%

Procedure

Acrylic acid chloride (996 mg, 11 mmol) was added dropwise within 5 min to a stirred suspension of the bis-methoxyamine 3 (881 mg, 5 mmol), Na2CO3 (2.65 g, 25 mmol) and BHT (=2,6-tert-butyl-4-methylphenol) (10 mg) in anhydrous diethylether (100 ml) accompanied by ice-cooling. The reaction mixture was then left to heat up to room temperature and stirred for a further 16 h. After the bis-methoxyamine 3 was completely consumed, water (20 ml) was added, the organic phase separated off and the aqueous phase extracted with diethyl ether (3×20 ml). The organic phases were combined, the solvent removed under vacuum and the crude product purified using column chromatography (silica gel, eluent chloroform/ethyl acetate 3:1). 1.1 g (79%) 1,6-bis(N-acryloyl-N-methoxyamino)hexane 4 was obtained. 1H-NMR (300 MHz, CDCl3): δ=1.31-1.36 (m, 4H), 1.59-1.69 (m, 4H), 3.65 (t, J=7.2 Hz, 4H), 3.68 (s, 6H), 5.74 (dd, J=10.3, 2.1 Hz, 2H), 6.41 (dd, J=17.1, 2.1 Hz, 2H), 6.71 (dd, J=17.1, 10.3 Hz, 2H) ppm. 13C-NMR (75 MHz, CDCl3): δ=26.4 (2CH2), 26.9 (2CH2), 44.9 (2CH2), 62.1 (2CH3), 126.2 (CH), 128.9 (CH2), 166.1 (2C) ppm.

Workup

  1. temperaturecooling
  2. waitThe reaction mixture was then left
  3. customAfter the bis-methoxyamine 3 was completely consumed
  4. additionwater (20 ml) was added
  5. customthe organic phase separated off
  6. extractionthe aqueous phase extracted with diethyl ether (3×20 ml)
  7. customthe solvent removed under vacuum
  8. customthe crude product purified

Sources & evidence

ORD record
ord-2b4356e21dcd404f88f2e67fc79be87a
Source dataset
uspto-grants-2014_11
Patent number
US08883877B2

Reaction notes

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