1,6-Hexanediol → HCID 131721651, compound

HRID 368920Notes

Reaction equation

HRID 368920 reaction equation
[CH2:1]([OH:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][OH:7].[C:9]([N:12]1[C:16](=[O:17])[CH:15]=[CH:14][C:13]1=[O:18])(=[O:11])[NH2:10]>C(#N)C.[Cl-].[Zn+2].[Cl-]>[C:16]([O:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:1][O:8][C:16](=[O:17])/[CH:15]=[CH:14]\[C:13](=[O:18])[NH:12][C:9](=[O:11])[NH2:10])(=[O:17])/[CH:15]=[CH:14]\[C:13](=[O:18])[NH:12][C:9](=[O:11])[NH2:10]

Participants

5

Reactant 2

HCID 123741,6-HexanediolHCID 76868N-Carbamylmaleimide

Product 1

HCID 131721651HCID 131721651, compoundYield 70.6%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

A mixture of 5.66 g of 1,6-hexanediol (0.048 moles), 12 g of N-carbamylmaleimide (0.086 moles) and 0.3 g of zinc chloride (0.0022 moles) in 70 mL of acetonitrile was heated to reflux. After 3 hours, a lot of solid material had been produced from the mixture. The mixture was filtered and the solids washed with acetonitrile and dried to afford 12.1 g of 1,6-hexanediol bismaleurate.

Workup

  1. temperaturewas heated to reflux
  2. customa lot of solid material had been produced from the mixture
  3. filtrationThe mixture was filtered
  4. washthe solids washed with acetonitrile
  5. customdried

Sources & evidence

ORD record
ord-bdaa163f720c4892bd85a72b7044531c
Source dataset
uspto-grants-2000_10
Patent number
US06136378

Reaction notes

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