Acetic Anhydride → HCID 20148554, compound

HRID 569063Notes

Reaction equation

HRID 569063 reaction equation
CN(C)C=[N:4][S:5]([C:8]1[S:17][C:11]2=[N+:12]([O-])[CH:13]=[CH:14][CH:15]=[C:10]2[CH:9]=1)(=[O:7])=[O:6].C(OC(=O)C)(=[O:21])C>O>[S:5]([C:8]1[S:17][C:11]2[NH:12][C:13](=[O:21])[CH:14]=[CH:15][C:10]=2[CH:9]=1)(=[O:7])(=[O:6])[NH2:4]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 54461528HCID 54461528, compound

Product 1

HCID 20148554HCID 20148554, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of the product from Step A (10.75 g, 0.038 mol) and 50 ml of acetic anhydride was heated at reflux for 16 hours. After removal of the acetic anhydride in vacuo, the residue was heated in 6 N hydrochloric acid (50 ml) for 3 hours. The cooled reaction mixture was diluted with water (400 ml), chilled and the resulting solid was filtered, washed with water and dried, 5.25 g (60% yield). Recrystallization from water gave 2-sulfamoylthieno[2,3-b]pyridin-6(7H)-one; m.p. 306°-308° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 16 hours
  3. customAfter removal of the acetic anhydride in vacuo
  4. temperaturethe residue was heated in 6 N hydrochloric acid (50 ml) for 3 hours
  5. customThe cooled reaction mixture
  6. temperaturechilled
  7. filtrationthe resulting solid was filtered
  8. washwashed with water
  9. customdried
  10. customRecrystallization from water

Sources & evidence

ORD record
ord-353eaf0330a24f47abe83109a90eed8a
Source dataset
uspto-grants-1988_03
Patent number
US04731368

Reaction notes

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