Acetic Acid → 8-Hydroxydibenzo[b,f]thiepin-3-carboxylic Acid-5-Oxide

HRID 485466Notes

Reaction equation

HRID 485466 reaction equation
C(C1[CH:4]=[CH:5][C:6]2[CH:12]=[CH:11][C:10]3[CH:13]=[C:14]([OH:17])[CH:15]=[CH:16][C:9]=3[S:8](=[O:18])[C:7]=2[CH:19]=1)#N.[OH-].[Na+].[C:22]([OH:25])(=[O:24])[CH3:23]>>[OH:17][C:14]1[CH:15]=[CH:16][C:9]2[S:8](=[O:18])[C:7]3[CH:19]=[C:23]([C:22]([OH:25])=[O:24])[CH:4]=[CH:5][C:6]=3[CH:12]=[CH:11][C:10]=2[CH:13]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 134903853-Cyano-8-hydroxydibenzo[b,f]thiepin-5-Oxide

Product 1

HCID 134903868-Hydroxydibenzo[b,f]thiepin-3-carboxylic Acid-5-Oxide

Procedure

Suspend 100 mg. of the cyano compound of Step 2 in 5 ml. of acetic acid and 5 ml. of 20% aqueous sodium hydroxide. Reflux under nitrogen for 1 hour. Evaporate the alcohol and dilute the residue with water. Extract with ether and acidify the aqueous phase with 6N hydrochloric acid. Separate the solids by filtration. Dissolve the solids in ethanol and strip to dryness to obtain the title product (m.p., 288°-291° C. dec.).

Workup

  1. temperatureReflux under nitrogen for 1 hour
  2. customEvaporate the alcohol
  3. additiondilute the residue with water
  4. extractionExtract with ether
  5. customSeparate the solids
  6. filtrationby filtration
  7. dissolutionDissolve the solids in ethanol

Sources & evidence

ORD record
ord-189e32b90e764de18a5b621f219d5298
Source dataset
uspto-grants-1985_08
Patent number
US04536507

Reaction notes

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