Acetic Anhydride → 2-Cyanophenoxathiin

HRID 2398780Notes

Reaction equation

HRID 2398780 reaction equation
[CH:1]1[C:14]2[S:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[O:6][C:5]=2[CH:4]=[CH:3][C:2]=1[CH:15]=O.Cl.[NH2:18]O.C([O-])(=O)C.[Na+].C(OC(=O)C)(=O)C>C(O)(=O)C>[C:15]([C:2]1[CH:3]=[CH:4][C:5]2[O:6][C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[S:13][C:14]=2[CH:1]=1)#[N:18]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 6150472-Formylphenoxathin

Product 1

HCID 203841882-Cyanophenoxathiin

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The crude phenoxathiin-2-aldehyde was dissolved in acetic acid (150 ml) and boiled with hydroxylamine hydrochloride (2.76 g) and sodium acetate (3.24 g) for 1.5 hr. Acetic anhydride (150 ml) was added, and the mixture boiled under reflux for 3 hr., cooled and filtered. The filtrate was poured into water and stirred for 1 hour to decompose the acetic anhydride, then extracted with chloroform, washed with water and sodium bicarbonate solution, dried, and evaporated to give crude 2-cyanophenoxathiin as an oil which solidified.

Workup

  1. temperatureunder reflux for 3 hr
  2. temperature, cooled
  3. filtrationfiltered
  4. additionThe filtrate was poured into water
  5. extractionextracted with chloroform
  6. washwashed with water and sodium bicarbonate solution
  7. customdried
  8. customevaporated

Sources & evidence

ORD record
ord-670fd27f8d0a44ad9b67a05e8b00b074
Source dataset
uspto-grants-1977_05
Patent number
US04025635

Reaction notes

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