Formaldehyde → HCID 135524538, compound

HRID 1493032Notes

Reaction equation

HRID 1493032 reaction equation
N[C:2]1[N:6]=[C:5]([C:7]2[CH:12]=[C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:10]([OH:17])=[C:9]([C:18]([CH3:21])([CH3:20])[CH3:19])[CH:8]=2)[O:4][N:3]=1.C=O.[C:24]([BH3-])#[N:25].[Na+].[C:28](=O)([O-])[O-].[Na+].[Na+]>C(O)(=O)C>[CH3:28][N:25]([CH3:24])[C:2]1[N:6]=[C:5]([C:7]2[CH:12]=[C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:10]([OH:17])=[C:9]([C:18]([CH3:21])([CH3:20])[CH3:19])[CH:8]=2)[O:4][N:3]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 10340Sodium CarbonateHCID 5003444Sodium cyanoborohydrideHCID 135400958HCID 135400958, compound

Product 1

HCID 135524538HCID 135524538, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stirred mixture of 2.0 g (0.0069 mole) of 4-(3-amino-1,2,4-oxadiazol-5-yl)-2,6-bis(1,1-dimethylethyl)phenol and 2.0 g (0.0067 mole) of paraformaldehyde in 45 ml of glacial acetic acid (under a nitrogen atmosphere) is added 2.0 g (0.032 mole) of sodium cyanoborohydride, in portions over ten minutes. The mixture is stirred at room temperature for 24 hours, then cooled in ice and treated cautiously with 250 ml of ice water. Solid sodium carbonate is added until the reaction mixture becomes slightly basic. The mixture is extracted with ethyl acetate (4×100 ml), and the combined organic layers are washed with brine (2×200 ml), dried (anhydrous sodium sulfate), and evaporated. Recrystallization of the residue from aqueous methanol yields 1.0 g (45% yield) of the analytically pure product, mp 135°-138°.

Workup

  1. waitin portions over ten minutes
  2. temperaturecooled in ice
  3. extractionThe mixture is extracted with ethyl acetate (4×100 ml)
  4. washthe combined organic layers are washed with brine (2×200 ml)
  5. dry with materialdried (anhydrous sodium sulfate)
  6. customevaporated
  7. customRecrystallization of the residue from aqueous methanol
  8. customyields 1.0 g (45% yield) of the analytically pure product, mp 135°-138°

Sources & evidence

ORD record
ord-b4b30b20e5d64c38898337a3bf6be847
Source dataset
uspto-grants-1994_12
Patent number
US05376670

Reaction notes

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