Trimethylolpropane → HCID 86755166, compound

HRID 368918Notes

Reaction equation

HRID 368918 reaction equation
[CH2:1]([C:3]([CH2:8][OH:9])([CH2:6][OH:7])[CH2:4][CH3:5])[OH:2].[C:10]([N:13]1[C:17](=[O:18])[CH:16]=[CH:15][C:14]1=[O:19])(=[O:12])[NH2:11]>C(#N)C.[Cl-].[Zn+2].[Cl-]>[C:14]([OH:19])(=[O:2])/[CH:15]=[CH:16]\[C:17](=[O:18])[NH:13][C:10](=[O:12])[NH2:11].[C:14]([OH:19])(=[O:2])/[CH:15]=[CH:16]\[C:17](=[O:18])[NH:13][C:10](=[O:12])[NH2:11].[C:14]([OH:19])(=[O:2])/[CH:15]=[CH:16]\[C:17](=[O:18])[NH:13][C:10](=[O:12])[NH2:11].[CH2:1]([C:3]([CH2:8][OH:9])([CH2:6][OH:7])[CH2:4][CH3:5])[OH:2]

Participants

5

Reactant 2

HCID 6510TrimethylolpropaneHCID 76868N-Carbamylmaleimide

Product 1

HCID 86755166HCID 86755166, compoundYield 361.5%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

A mixture of 9.86 g of trimethylolpropane (0.074 moles), 31.3 g of N-carbamylmaleimide (0.224 moles) and 0.85 g of zinc chloride (0.00625 moles) in 215 mL of acetonitrile was heated to reflux. After 5 hours, the acetonitrile was evaporated to afford 40.7 g of trimethylolpropane trimaleurate as a white solid. M.P.: 70°-76° C.; 1H NMR (DMSO-d6): δ 10.5 (s, 3 H), 7.2-7.7 (m, 6 H), 6.3-6.6 (m, 6 H), 4.1 (s, 6 H), 1.35 (q, 2 H), 1.85 (t, 3 H).

Workup

  1. temperaturewas heated to reflux
  2. customthe acetonitrile was evaporated

Sources & evidence

ORD record
ord-c39a69d3b11d44e6b9d3c59e4981f6c0
Source dataset
uspto-grants-2000_10
Patent number
US06136378

Reaction notes

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