Hydrochloric Acid → HCID 178436646, compound

HRID 1417136Notes

Reaction equation

HRID 1417136 reaction equation
C(N(CC)CC)C.Cl[S:9]([C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[O:18][C:17](=[O:22])[C:16](=[N+:23]=[N-:24])[C:15]2=[O:25])(=[O:11])=[O:10].Cl.C1C[O:30]CC1>>[CH2:16]=[CH:15][C:14]1[CH:19]=[CH:20][C:21]([OH:30])=[CH:12][CH:13]=1.[N+:23](=[C:16]1[C:15](=[O:25])[C:14]2[C:19](=[CH:20][CH:21]=[C:12]([S:9]([O-:30])(=[O:11])=[O:10])[CH:13]=2)[O:18][C:17]1=[O:22])=[N-:24]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 8028Tetrahydrofuran2×HCID 8471TriethylamineHCID 178514331HCID 178514331, compound

Product 1

HCID 178436646HCID 178436646, compoundYield 1,032.7%

Conditions

Temperature
12 °C

Procedure

The Example 12 illustrates the preparation of a partially substituted polymeric product with a photoactive compound. Example 7 was substantially repeated in Example 12 with the exception of modifications in procedure as set forth below. A 500 ml three-necked round-bottom flask equipped with a magnetic stirrer, water bath, thermometer, nitrogen inlet and bubbler was charged with a solution of poly-4-hydroxystyrene (13.3 g, 110 mmol based on monomer repeat units) in THF (170 g). Triethylamine (6.8 g) was added dropwise and the reaction mixture was allowed to stir for an additional 3-5 minutes. A solution of 6-chlorosulfonyl-3-diazo-4-oxocoumarin (1.6 g, 5.6 mmol) in THF (124 g) was added dropwise and the reaction was allowed to stir at room temperature. After one hour, HPLC analysis showed no residual starting material. The reaction mixture was cooled in an ice bath and neutralized by dropwise addition of conc. HCl (8 g) while maintaining the reaction temperature around 12° C. The reaction mixture was filtered to remove any insoluble impurities. The filtrate was precipitated, with stirring, into ten times its weight of hexane. The resulting slurry was filtered, dried in a vacuum oven overnight at 60° C.; yield 11.2 g of white solids (77% yield).

Workup

  1. customthe preparation of a partially substituted polymeric product with a photoactive compound
  2. customA 500 ml three-necked round-bottom flask equipped with a magnetic stirrer, water bath
  3. stirringto stir at room temperature
  4. waitAfter one hour
  5. temperatureThe reaction mixture was cooled in an ice bath
  6. filtrationThe reaction mixture was filtered
  7. customto remove any insoluble impurities
  8. customThe filtrate was precipitated
  9. stirringwith stirring, into ten times its weight of hexane
  10. filtrationThe resulting slurry was filtered
  11. customdried in a vacuum oven overnight at 60° C.

Sources & evidence

ORD record
ord-6ae6142c35f7478cbaff39f8404846e6
Source dataset
uspto-grants-1999_03
Patent number
US05876897

Reaction notes

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