Water → HCID 57483902, compound

HRID 381697Notes

Reaction equation

HRID 381697 reaction equation
[CH2:1]([OH:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[C:18]([N:21]1[C:25](=[O:26])[CH:24]=[CH:23][C:22]1=[O:27])(=[O:20])[NH2:19].O>O1CCOCC1.[Cl-].[Zn+2].[Cl-]>[C:25]([O:17][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])(=[O:26])/[CH:24]=[CH:23]\[C:22](=[O:27])[NH:21][C:18](=[O:20])[NH2:19]

Participants

6

Reactant 3

HCID 962WaterHCID 2682Cetyl AlcoholHCID 768681H-Pyrrole-1-carboxamide, 2,5-dihydro-2,5-dioxo- (9CI)

Product 1

HCID 57483902HCID 57483902, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 49 g of hexadecanol (0.202 moles), 28 g of N-carbamylmaleimide (0.2 moles) and 270 mg of zinc chloride (0.002 moles) in 300 mL of p-dioxane was heated to reflux. After 24 hours, the mixture was cooled to room temperature and 200 mL of H2O was added. The resulting solid was filtered, washed with additional H2O and dried to afford 75 g (97% yield) of hexadecyl maleurate. M.P.: 106°-09° C. (dec.); 1H NMR (CDCl3): δ10.5 (br s, 1H), 8.2 (br s, 1H), 6.3 (m, 2H), 5.4 (br s, 1H), 4.2 (t, 2H), 1.6 (m, 2 H), 1.2 (m, 26H), 0.9 (t, 3H); HPLC (80% CH3CN/H2O, C18): Rt=6.9 minutes.

Workup

  1. temperaturewas heated to reflux
  2. filtrationThe resulting solid was filtered
  3. washwashed with additional H2O
  4. customdried

Sources & evidence

ORD record
ord-b9e9550ce8b9406495232430735ba4b9
Source dataset
uspto-grants-2001_10
Patent number
US06307058B1

Reaction notes

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