Water → 4-ethyl-2-p-tolyl-5,6-dihydro-4H-1,3-selenazin-4-ol

HRID 788

Reaction equation

HRID 788 reaction equation
[C:1]([O:9][CH2:10][CH:11](CC)[CH2:12][CH:13]([OH:16])[CH2:14][CH3:15])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[CH2:20]1[CH2:24]OC(N2C(=O)NC(=O)C(F)=C2)[CH2:21]1.[CH3:34][CH2:35][C:36]1([OH:49])[N:41]=[C:40]([C:42]2[CH:47]=[CH:46][C:45]([CH3:48])=[CH:44][CH:43]=2)[Se:39][CH2:38][CH2:37]1>C(OCC)(=O)C>[C:1]([O:9][CH2:10][CH2:11][CH2:12][CH:13]([OH:16])[CH2:14][CH2:15][CH2:21][CH2:20][CH3:24])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1.[CH3:34][CH2:35][C:36]1([OH:49])[N:41]=[C:40]([C:42]2[CH:47]=[CH:46][C:45]([CH3:48])=[CH:44][CH:43]=2)[Se:39][CH2:38][CH2:37]1

Participants

7

Reactant 4

HCID 962Water3×HCID 5386Tegafur2×HCID 99038694-ethyl-2-p-tolyl-5,6-dihydro-4H-1,3-selenazin-4-ol4×HCID 571458574-Hydroxy-(2'-ethylhexyl) benzoate

Product 2

HCID 99038694-ethyl-2-p-tolyl-5,6-dihydro-4H-1,3-selenazin-4-olHCID 543654304-Hydroxy-nonyl benzoate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A comparison thermal solvent dispersion 4-hydroxy-(2'-ethylhexyl) benzoate (TS-1), a liquid at room temperature, is prepared by similar means. An aqueous solution of 10% (w/w) aqueous DA-9 (6 g), 8.3% aqueous gelatin (about 54 g), and water (74.9 g) is combined with 15 g TS-1, stirred, passed through a colloid mill 5 times, chill set, and stored in the cold until it is used for melt preparation. This colloid milled dispersion is designated a TS-1 CM dispersion. A solid particle thermal solvent dispersion of 4-hydroxy-nonyl benzoate (TS-2; Pfaltz and Bauer; melting point 90°-93° C.) is prepared similarly. About 12 g of TS-2 was dissolved in 24 g of ethyl acetate and mixed with an aqueous gelatin solution comprising 4.8 g of 10% (w/w) aqueous DA-9, 43.3 g of 8.3% (w/w) aqueous gelatin, and 35.9 g of water to give a crude dispersion. This dispersion is passed through a colloid mill 5 times, chill set, noodled, washed to remove ethyl acetate, remelted, chill set, and stored in the cold until used for melt preparation. This colloid milled dispersion is designated TS-2 (CM). Another solid particle thermal solvent dispersion of TS-2 is prepared by roller milling methods. About 18 g of TS-2 is combined with 36 g of 10% aqueous DA-9 , 66 g of water, and about 100 mL of 1.8-2.1 mm-diameter zirconia milling media and placed in a sealed glass jar. This jar is placed on a roller mill for about 123 hours, and a fine particle sized aqueous dispersion is obtained. This dispersion is passed through a cloth filter. About 110 g of this filtrate is combined with about 55.3 g of 8.3% (w/w) aqueous gelatin and 1.9 g of water at about 40° C., stirred, chill set, and stored in the cold until it is used for melt preparation. This roller milled dispersion is designated TS-2 RM.

Workup

  1. temperaturechill set
  2. customis used for melt preparation
  3. additionmixed with an aqueous gelatin solution
  4. customto give a crude dispersion
  5. temperaturechill set
  6. washwashed
  7. customto remove ethyl acetate
  8. temperaturechill set
  9. customuntil used for melt preparation
  10. customis obtained
  11. filtrationfilter
  12. customis combined with about 55.3 g of 8.3% (w/w) aqueous gelatin and 1.9 g of water at about 40° C.
  13. stirringstirred
  14. temperaturechill set
  15. customis used for melt preparation
  16. customThis roller milled dispersion

Sources & evidence

ORD record
ord-3c799edf560b44e4b1b3a6fde9733781
Source dataset
uspto-grants-1998_03
Patent number
US05723255

Linked notes

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