Acetic Acid → HCID 20279315, compound

HRID 1248284Notes

Reaction equation

HRID 1248284 reaction equation
[CH3:1][C:2]1[C:14](N)=[CH:13][CH:12]=[CH:11][C:3]=1[O:4][CH:5]([CH3:10])[C:6]([O:8][CH3:9])=[O:7].[C:16](O)(=O)C.C=O.[C:22]([BH3-])#[N:23].[Na+]>C(#N)C>[CH3:1][C:2]1[C:14]([N:23]([CH3:22])[CH3:16])=[CH:13][CH:12]=[CH:11][C:3]=1[O:4][CH:5]([CH3:10])[C:6]([O:8][CH3:9])=[O:7]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 20279319HCID 20279319, compound

Product 1

HCID 20279315HCID 20279315, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 7.7 g (ca. 37 mmole) of the title product of Example 18, 2.1 ml of acetic acid, 30 ml of 37% formaldehyde, and 50 ml of acetonitrile was added 2.3 g (37 mmole) of sodium cyanoborohydride. After the amino compound had been consumed, aqueous sodium hydroxide was added and the mixture extracted with diethyl ether. The organic phase was washed with water, dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was chromatographed on silica gel using ethyl acetate-hexane as eluent, giving the title compound (4.2 g) as an oil. The compound was used in subsequent reeactions without further purification.

Workup

  1. customAfter the amino compound had been consumed
  2. additionaqueous sodium hydroxide was added
  3. extractionthe mixture extracted with diethyl ether
  4. washThe organic phase was washed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-9f8db783f3684f50a0a666b2d9d490c8
Source dataset
uspto-grants-1985_06
Patent number
US04523020

Reaction notes

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