Formaldehyde → HCID 178481284, compound

HRID 1290997Notes

Reaction equation

HRID 1290997 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([OH:8])[CH2:4][CH2:3]1.[CH3:9][N:10](C)[C:11](N)=O.C=[O:16].[CH3:17][N:18]1[CH2:23]COC[CH2:19]1>C1(C)C=CC=CC=1.O1CCOCC1>[OH:8][C@H:5]1[CH2:6][CH2:7][C@H:2]([N:1]2[CH2:9][N:10]([CH3:11])[C:23](=[O:16])[N:18]([CH3:17])[CH2:19]2)[CH2:3][CH2:4]1

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 79724-MethylmorpholineHCID 11737N,N-DimethylureaHCID 178511715HCID 178511715, compound

Product 1

HCID 178481284HCID 178481284, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a mixture of trans-4-aminocyclohexanol (5.00 g, 43.4 mmol), N,N-dimethylurea (3.82 g, 43.4 mmol), 37% formalin (50 ml), N-methylmorpholine (9.54 ml, 86.8 mmol) and dioxane (10 ml) was added toluene (200 ml), and the mixture was heated for about 5 hours while removing water for azeotropic distillation. Low boiling matters were distilled away from the reaction mixture under reduced pressure, and the residue was purified by silica gel column chromatography (methylene chloride/methanol=50/1-10/1) to give 7.40 g of trans-5-(4-hydroxycyclohexyl)-1,3-dimethylhexahydro-2-oxo-1,3,5-triazine as colorless solid (75%).

Workup

  1. temperaturethe mixture was heated for about 5 hours
  2. customwhile removing water
  3. distillationfor azeotropic distillation
  4. distillationwere distilled away from the reaction mixture under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (methylene chloride/methanol=50/1-10/1)

Sources & evidence

ORD record
ord-6c42842c47cc4db78bd37a9ead13f8bc
Source dataset
uspto-grants-1998_05
Patent number
US05753670

Reaction notes

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