Pyridine → Benzoxazole

HRID 1994663Notes

Reaction equation

HRID 1994663 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC12CC3(C45CC6(C)CC(C)(CC(C(Cl)=O)(C6)C4)C5)CC(C)(CC([C:34](Cl)=[O:35])(C3)C1)C2.[C:37]1(C#CC2C=C(C(Cl)=O)C=C(C=2)C(Cl)=O)C=CC=CC=1.C(Cl)(=O)C1C=CC=CC=1>CN1CCCC1=O.O>[O:35]1[C:34]2[CH:2]=[CH:3][CH:4]=[CH:5][C:6]=2[N:1]=[CH:37]1

Participants

7

Reactant 4

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 12080909HCID 12080909, compoundHCID 87425722HCID 87425722, compound

Product 1

HCID 9228Benzoxazole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
60 °C

Procedure

In a 2 L four-neck flask provided with a thermometer, a Dimroth condenser and an agitator, 64.8 g of 4,6-di(3,5-dimethyl-1-adamantyl)-1,3-bis(4-amino-3-hydroxyphenoxy)benzene (0.10 mol) obtained in Synthesis example 2 was dissolved in 800 g of dried N-methyl-2-pyrrolidone under nitrogen flow followed by the addition of 17.4 g of pyridine (0.22 mol). The mixture was heated to 60° C. and 31.6 g of 5,5′,7,7′-tetramethyl-1,1′-biadamantane-3,3′-dicarboxylic acid chloride (0.070 mol) was gradually added and then agitated at 60° C. for three hours. 7.57 g of 5-phenylethynyl-isophthalic acid chloride (0.025 mol) was gradually added with the inner temperature of the flask kept at 5° C. or below in an ice bath. Then, 2.10 g of benzoic acid chloride (0.015 mol) was added with the inner temperature of the flask kept at 5° C. or below. A reaction solution was added to 4 L of distilled water in small droplets followed by collecting and drying precipitate, thus obtaining a benzoxazole resin precursor.

Workup

  1. customkept at 5° C. or below in an ice bath
  2. customkept at 5° C. or below
  3. customby collecting
  4. customdrying precipitate

Sources & evidence

ORD record
ord-e9e8179feb53407d97fc521d863564a5
Source dataset
uspto-grants-2010_01
Patent number
US07652125B2

Reaction notes

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