Ethyl orthoformate → HCID 136038673, compound

HRID 1493037Notes

Reaction equation

HRID 1493037 reaction equation
[NH2:1][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.[CH:22](OCC)(OCC)[O:23][CH2:24][CH3:25]>>[CH3:16][C:13]([C:11]1[CH:12]=[C:7]([C:5]2[O:4][N:3]=[C:2]([N:1]=[CH:22][O:23][CH2:24][CH3:25])[N:6]=2)[CH:8]=[C:9]([C:18]([CH3:21])([CH3:20])[CH3:19])[C:10]=1[OH:17])([CH3:14])[CH3:15]

Participants

3

Reactant 2

HCID 31214Ethyl orthoformateHCID 135400958HCID 135400958, compound

Product 1

HCID 136038673HCID 136038673, compoundYield 67.5%

Procedure

A mixture of 0.87 g (0.003 mole) of 4-(3-amino-1,2,4-oxadiazol-5-yl)-2,6-bis(1,1-dimethylethyl)phenol and 25 ml (22.3 g; 0.15 mole) of anhydrous triethyl orthoformate is stirred at reflux (under a nitrogen atmosphere) for 24 hours. The cooled mixture is evaporated, and the residue is distributed between 75 ml of dichloromethane and 100 ml of saturated aqueous sodium bicarbonate solution. The aqueous layer is extracted several times with fresh dichloromethane, and the combined organic layers are washed with brine. The organic layer is dried (anhydrous sodium sulfate) and evaporated. Recrystallization of the residue from aqueous acetonitrite yields 0.70 g (67% yield) of ethyl N-[5-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]-1,2,4-oxadiazol-3-yl]methanimidoate, mp 159°-161° C.

Workup

  1. temperatureat reflux (under a nitrogen atmosphere) for 24 hours
  2. customThe cooled mixture is evaporated
  3. extractionThe aqueous layer is extracted several times with fresh dichloromethane
  4. washthe combined organic layers are washed with brine
  5. dry with materialThe organic layer is dried (anhydrous sodium sulfate)
  6. customevaporated
  7. customRecrystallization of the residue from aqueous

Sources & evidence

ORD record
ord-0c410f337c7840ca8870a5aec6e091a1
Source dataset
uspto-grants-1994_12
Patent number
US05376670

Reaction notes

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