Methylglyoxal → HCID 11298738, compound

HRID 1443025Notes

Reaction equation

HRID 1443025 reaction equation
[CH:1](=O)[C:2]([CH3:4])=O.[NH2:6][CH2:7][CH2:8][NH:9][CH2:10][CH2:11][NH:12][CH2:13][CH2:14][NH2:15].N1[C:20]2C=CC=C[C:19]=2N=N1.C(C=O)=O.[BH4-].[Na+]>O.CO>[CH3:4][C:2]12[CH:1]3[N:6]4[CH2:19][CH2:20][N:15]3[CH2:14][CH2:13][N:12]1[CH2:11][CH2:10][N:9]2[CH2:8][CH2:7]4

Participants

8

Reactant 5

HCID 880MethylglyoxalHCID 5565TriethylenetetramineHCID 7860GlyoxalHCID 4311764Sodium borohydrideHCID 178418385HCID 178418385, compound

Product 1

HCID 11298738HCID 11298738, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent3×

Conditions

Temperature
2 °C

Procedure

A 40% strength solution of 61.53 g of pyruvaldehyde in water (341.8 mmol) in 20 ml of water is added by slow dropwise addition INto a solution of 50 g (341.8 mmol) of triethylenetetraamine in 800 ml of distilled water cooled to 2° C. On completion of addition, the reaction mixture is adjusted to ambient temperature and 81.36 g (683.6 mmol) of benzotriazole are added in a single portion. A solution of glyoxal (40% in water) (341.8 mmol) in 200 ml of methanol is then added by slow dropwise addition. After 2 h of stirring at ambient temperature, 25.85 g (683.6 mmol) of NaBH4 are added in small portions. After 2 h of stirring at ambient temperature, the methanol is evaporated and 50 g of KOH pellets are added to the residue. The solution is then extracted with three 1.5 l portions of chloroform. After drying over MgSO4 and evaporation of the solvents, (IIb) is isolated in the form of an orange oil (28.50 g; yield=40%).

Workup

  1. additionOn completion of addition
  2. customis adjusted to ambient temperature
  3. stirringAfter 2 h of stirring at ambient temperature
  4. customthe methanol is evaporated
  5. addition50 g of KOH pellets are added to the residue
  6. extractionThe solution is then extracted with three 1.5 l portions of chloroform
  7. dry with materialAfter drying over MgSO4 and evaporation of the solvents
  8. custom(IIb) is isolated in the form of an orange oil (28.50 g; yield=40%)

Sources & evidence

ORD record
ord-abb7738ca13944a39b9006034db7d773
Source dataset
uspto-grants-2010_02
Patent number
US07659393B2

Reaction notes

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