Hydrochloric Acid → HCID 12788615, compound

HRID 1680652Notes

Reaction equation

HRID 1680652 reaction equation
C(O)(=O)C.C(O)(=O)C.[CH2:9]([O:11][C:12]([C:14]1[CH:23]=[C:22]([OH:24])[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([NH:25][C:26]([C:28]3[CH:29]=[C:30]([NH:34][C:35](=[O:62])[NH:36][C:37]4[CH:42]=[CH:41][CH:40]=[C:39]([C:43]([NH:45][C:46]5[CH:47]=[C:48]6[C:53](=[CH:54][CH:55]=5)[CH:52]=[C:51]([C:56]([O:58][CH2:59][CH3:60])=[O:57])[CH:50]=[C:49]6[OH:61])=[O:44])[CH:38]=4)[CH:31]=[CH:32][CH:33]=3)=[O:27])[CH:20]=2)[CH:15]=1)=[O:13])[CH3:10].CN(C)C=O.[OH-].[Na+].Cl>O.N1C=CC=CC=1>[CH2:9]([O:11][C:12]([C:14]1[CH:23]=[C:22]([OH:24])[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([NH:25][C:26]([C:28]3[CH:29]=[C:30]([NH:34][C:35](=[O:62])[NH:36][C:37]4[CH:42]=[CH:41][CH:40]=[C:39]([C:43]([NH:45][C:46]5[CH:47]=[C:48]6[C:53](=[CH:54][CH:55]=5)[CH:52]=[C:51]([C:56]([O:58][CH2:59][CH3:60])=[O:57])[CH:50]=[C:49]6[OH:61])=[O:44])[CH:38]=4)[CH:31]=[CH:32][CH:33]=3)=[O:27])[CH:20]=2)[CH:15]=1)=[O:13])[CH3:10]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 86737812HCID 86737812, compound

Product 1

HCID 12788615HCID 12788615, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 1049PyridineSolvent

Procedure

To a cooled (water bath) solution of 2.0 g. of 6,6'-[ureylenebis(m-phenylenecarbonylimino)]bis[4-hydroxy-2-naphthoic acid] diethyl ester diacetate in 60 ml. of dimethylformamide is added 40 ml. of 0.25 N sodium hydroxide, dropwise with stirring over 10 minutes. The solution is stirred for an additional 10 minutes, 80 ml. of pyridine is added and the solution is poured with cooling into a mixture of 800 ml. of water and 85 ml. of concentrated hydrochloric acid. The solid is collected by filtration, washed with water and dried at room temperature. This solid is dissolved in hot 2-methoxyethanol at a concentration of 4% (w/v). This solution is then distilled with 1/2 its volume of water and then cooled to room temperature. The precipitate is collected by filtration and washed with 50% aqueous 2-methoxyethanol, ethanol, then ether. This solid is dissolved in a mixture of 2-methoxyethanol:dimethylformamide (6.5:1) giving an approximate 4% (w/v) solution, diluted with water and filtered. The solid is washed as described above, then with acetone and dried at 110° C., overnight giving 417 mg. of the desired product as a tan powder, m.p. 265°-280° C. (dec.).

Workup

  1. additionthe solution is poured
  2. temperaturewith cooling into a mixture of 800 ml
  3. filtrationThe solid is collected by filtration
  4. washwashed with water
  5. customdried at room temperature
  6. dissolutionThis solid is dissolved in hot 2-methoxyethanol at a concentration of 4% (w/v)
  7. distillationThis solution is then distilled with 1/2 its volume of water
  8. filtrationThe precipitate is collected by filtration
  9. washwashed with 50% aqueous 2-methoxyethanol, ethanol
  10. dissolutionThis solid is dissolved in a mixture of 2-methoxyethanol:dimethylformamide (6.5:1)
  11. customgiving an approximate 4% (w/v) solution
  12. filtrationfiltered
  13. washThe solid is washed
  14. customdried at 110° C., overnight
  15. customgiving 417 mg

Sources & evidence

ORD record
ord-be18a38c358d4bbf9b9500bf64d013ed
Source dataset
uspto-grants-1981_06
Patent number
US04275076

Reaction notes

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