Sulfuric Acid → HCID 3708133, compound

HRID 482679Notes

Reaction equation

HRID 482679 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([C:7]2[O:11][C:10]([C:12]3[CH:17]=[CH:16][C:15]([C:18]4[O:22][C:21]([C:23]5[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=5)=[CH:20][N:19]=4)=[CH:14][CH:13]=3)=[N:9][CH:8]=2)=[CH:3][CH:2]=1.[S:29](=[O:33])(=[O:32])([OH:31])O>>[C:12]1([C:10]2[O:11][C:7]([C:4]3[CH:3]=[CH:2][C:1]([S:29]([OH:33])(=[O:32])=[O:31])=[CH:6][CH:5]=3)=[CH:8][N:9]=2)[CH:17]=[CH:16][C:15]([C:18]2[O:22][C:21]([C:23]3[CH:28]=[CH:27][C:26]([S:29]([OH:31])(=[O:33])=[O:32])=[CH:25][CH:24]=3)=[CH:20][N:19]=2)=[CH:14][CH:13]=1

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 15732Oxazole, 2,2'-(1,4-phenylene)bis[5-phenyl-

Product 1

HCID 3708133HCID 3708133, compound

Procedure

One hundred milliliters of 20% fuming sulfuric acid (oleum) is charged into a 500 mL flask. Stirring is begun, and 50.0 g of POPOP is added in small portions. The reaction is exothermic. After the addition is complete, the reaction mixture is heated at about 90°-100°C. with stirring for two hours. The reaction is then quenched by pouring the reaction mixture onto 500 g of crushed ice with stirring. A bright-yellow product precipitates as a very fine powder. The resulting suspension is allowed to stand overnight. The product is then collected on a medium-porosity fritted-glass Buchner funnel. It should not be washed at this point, nor should the filter cake be disturbed. As much liquid is removed from the filter cake as possible. The pasty filter cake is then washed by stirring it in 200 mL of 2/1 (v/v) water/methanol or 1/20/10 concentrated hydrochloric acid/water/methanol. Water alone should not be used, as a very thick paste will form. Stirring is continued until the product is finely dispersed. The suspension is then allowed to settle briefly, and the solid is collected by vacuum filtration. The washing process should be repeated once. The product is then dried in a vacuum oven at 60°-70° C. Typical yields are 67-73 g (90-94%).

Workup

  1. additionAfter the addition
  2. temperaturethe reaction mixture is heated at about 90°-100°C.
  3. stirringwith stirring for two hours
  4. customThe reaction is then quenched
  5. additionby pouring the reaction mixture onto 500 g of crushed ice
  6. stirringwith stirring
  7. customA bright-yellow product precipitates as a very fine powder
  8. customThe product is then collected on a medium-porosity fritted-glass Buchner funnel
  9. washIt should not be washed at this point
  10. customAs much liquid is removed from the filter cake as possible
  11. washThe pasty filter cake is then washed
  12. stirringby stirring it in 200 mL of 2/1 (v/v) water/methanol or 1/20/10 concentrated hydrochloric acid/water/methanol
  13. customwill form
  14. stirringStirring
  15. additionis finely dispersed
  16. filtrationthe solid is collected by vacuum filtration
  17. customThe product is then dried in a vacuum oven at 60°-70° C
  18. customTypical yields

Sources & evidence

ORD record
ord-facba2c688b8435c9148a437f08a25a7
Source dataset
uspto-grants-1986_03
Patent number
US04575452

Reaction notes

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