Ethylene Oxide → HCID 14793571, compound

HRID 847421Notes

Reaction equation

HRID 847421 reaction equation
[CH:1]1[C:14]2[N:13]([C:15](Cl)=[O:16])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[S:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH2:18]1[O:20][CH:19]1[CH2:21][OH:22].O1CC1>>[CH:1]1[C:14]2[N:13]([C:15]([O:22][CH2:21][CH:19]3[O:20][CH2:18]3)=[O:16])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[S:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 6354Ethylene OxideHCID 11164GlycidolHCID 8786410H-Phenothiazine-10-carbonyl chloride

Product 1

HCID 14793571HCID 14793571, compound

Procedure

Phenothiazine N-carbonyl chloride, 1.5 g (6 mmol) and 6 mmol of glycidol were heated in a reflux apparatus equipped with a drying tube at 90° C. for 10 hours on an oil bath. Then the reflux apparatus was converted for distillation and the excess glycidol was removed under vacuum at this temperature. The resulting brown oil solidified upon cooling and was dissolved in chloroform, treated with charcoal, dried and evaporated to dryness. Recrystallization of the resulting solid from ethanol gave the product: 1.0 g (55%), tan crystals m.p. 92°-94° C. NMR: (CDCl3) 7.3, 8H, m, phenyl; 4.5, 2H, d, d, exocyclic --CH2 --; 3.4, 1H, m, CH; 2.9, 2H, m, endocyclic --CH2 --. IR: 1710, carbonyl; 1250, 900, oxirane; 750, aromatic.

Workup

  1. customequipped with a drying tube at 90° C. for 10 hours on an oil bath
  2. distillationThen the reflux apparatus was converted for distillation
  3. customthe excess glycidol was removed under vacuum at this temperature
  4. temperatureupon cooling
  5. dissolutionwas dissolved in chloroform
  6. additiontreated with charcoal
  7. customdried
  8. customevaporated to dryness
  9. customRecrystallization of the resulting solid from ethanol
  10. customgave the product

Sources & evidence

ORD record
ord-1a84bb7ea845441b80898f7a5a61f9ae
Source dataset
uspto-grants-1992_08
Patent number
US05142045

Reaction notes

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