Water → 3,4-dihydrothieno[3,2-f][1,4]thiazepin-5(2H)-one

HRID 847384Notes

Reaction equation

HRID 847384 reaction equation
[S:1]1[C:5]2[S:6][CH2:7][CH2:8][C:9](=[N:10]O)[C:4]=2[CH:3]=[CH:2]1.[OH2:12]>>[S:6]1[C:5]2[S:1][CH:2]=[CH:3][C:4]=2[C:9](=[O:12])[NH:10][CH2:8][CH2:7]1

Participants

3

Reactant 2

HCID 962WaterHCID 27397394H-Thieno[2,3-b]thiopyran-4-one, 5,6-dihydro-, oxime

Product 1

HCID 43659423,4-dihydrothieno[3,2-f][1,4]thiazepin-5(2H)-one

Procedure

To 300 g of polyphosphoric acid warmed at 70° C. was added 19.5 g of 5,6-dihydro-4H-thieno[2,3-b]thiopyran-4-one 4-oxime portionwise with stirring for 20 minutes. The mixture was stirred at 80° C. for 2.5 hours, poured into chilled water and extracted with chloroform. The extract was washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The resulting crude crystals were recrystallized from ethanol to give 10 g of 2,3-dihydrothieno[3,2-f]-1,4-thiazepin-5(4H)-one as white crystals, melting at 195°-196° C.

Workup

  1. stirringThe mixture was stirred at 80° C. for 2.5 hours
  2. additionpoured
  3. extractionextracted with chloroform
  4. washThe extract was washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting crude crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-33947bbe19144a7bbe461df9a64614ab
Source dataset
uspto-grants-1992_08
Patent number
US05141930

Reaction notes

Loading…