Iodine → HCID 67903394, compound

HRID 358732Notes

Reaction equation

HRID 358732 reaction equation
CN(C)[C:3](=[O:22])[CH:4]([CH2:19][CH:20]=[CH2:21])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].C1COCC1.[OH2:29].[I:30]I>C(OCC)(=O)C>[I:30][CH2:21][C@H:20]1[CH2:19][C@H:4]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[C:3](=[O:22])[O:29]1

Participants

5

Reactant 3

HCID 807IodineHCID 20066743N,N-dimethyl-2-allylhexadecanamideHCID 21881883Oxolane--water (1/1)

Product 1

HCID 67903394HCID 67903394, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 8.25 g (25.5 mmol) of N,N-dimethyl-2-allylhexadecanamide in THF/ H2O (1:3 v/v, 120 mL) 9.69 g (38.2 mmol) of iodine was added at room temperature and the reaction mixture was stirred for 3 days. Then, the mixture was diluted with 200 mL of ethyl acetate, washed twice with 10% sodium thiosulfate and extracted twice with ethyl acetate. The combined organic layers were dried with sodium sulfate and after evaporation of the solvent it was obtained 11.3 g of a solid that was purified by column chromatography (silica gel, hexane: ethyl acetate 7%) to give 6.98 g of the trans isomer, 0.91 g of a mixture of the cis and trans isomers and 0.42 g of the cis isomer (overall yield 87%).

Workup

  1. washwashed twice with 10% sodium thiosulfate
  2. extractionextracted twice with ethyl acetate
  3. dry with materialThe combined organic layers were dried with sodium sulfate
  4. customafter evaporation of the solvent it

Sources & evidence

ORD record
ord-e960e87dab8c491bbb95c5e1d7901ca7
Source dataset
uspto-grants-1991_03
Patent number
US04997843

Reaction notes

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