Cyanogen Bromide → HCID 10064427, compound

HRID 1029537Notes

Reaction equation

HRID 1029537 reaction equation
[CH3:1][C:2]([C:5]1[CH:6]=[C:7]([CH2:16][CH2:17][C:18]([NH:20][NH2:21])=[O:19])[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])[CH3:3].C(=O)(O)[O-].[Na+].[N:27]#[C:28]Br>O1CCOCC1.O.C(OCC)(=O)C>[NH2:27][C:28]1[O:19][C:18]([CH2:17][CH2:16][C:7]2[CH:6]=[C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[C:10]([OH:11])=[C:9]([C:12]([CH3:13])([CH3:14])[CH3:15])[CH:8]=2)=[N:20][N:21]=1

Participants

7

Reactant 3

HCID 10476Cyanogen BromideHCID 648653,5-Di-tert-butyl-4-hydroxyhydrocinnamic acid hydrazideHCID 516892Sodium Bicarbonate

Product 1

HCID 10064427HCID 10064427, compoundYield 59%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 3,5-bis(1,1-dimethylethyl)-4-hydroxybenzenepropanoic acid hydrazide (0.50 g, 1.71 mmol) in dioxane (15 mL) is added to a solution of sodium bicarbonate (0.16 g, 1.88 mmol) in water (4 mL). Cyanogen bromide (0.20 g, 1.88 mmol) is then added in 4 equal portions at 1-minute intervals, and stirring is continued for 5 hours. The reaction mixture is diluted with ethyl acetate and sequentially washed with aqueous sodium bicarbonate, water, and brine. Drying the organic phase over magnesium sulfate and evaporation provides a solid which is crystallized from ethyl acetate/hexane followed by methanol/water to give 0.32 g (59%) of 4-[2-(5-amino-1,3,4-oxadiazol-2-yl)ethyl]-2,6-bis(1,1-dimethylethyl)phenol, mp 220.0°-221.0° C.

Workup

  1. washsequentially washed with aqueous sodium bicarbonate, water, and brine
  2. customDrying the organic phase
  3. customover magnesium sulfate and evaporation
  4. customprovides a solid which
  5. customis crystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-3e4eb5a993b84878802b060f5960e043
Source dataset
uspto-grants-1992_04
Patent number
US05102897

Reaction notes

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