Water → HCID 22139417, compound

HRID 1825799Notes

Reaction equation

HRID 1825799 reaction equation
O.NN.[OH-].[K+].[CH3:6][O:7][C:8]1[C:18]2[S:17][C:16]3[CH:19]=[CH:20][CH:21]=[CH:22][C:15]=3[CH2:14][C:13](=O)[C:12]=2[CH:11]=[CH:10][CH:9]=1.O>C(O)CO>[CH3:6][O:7][C:8]1[C:18]2[S:17][C:16]3[CH:19]=[CH:20][CH:21]=[CH:22][C:15]=3[CH2:14][CH2:13][C:12]=2[CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 22139427HCID 22139427, compound

Product 1

HCID 22139417HCID 22139417, compound

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Conditions

Temperature
175 °C

Procedure

Hydrazine hydrate (4 ml) and potassium hydroxide (2.72 g, 48 mmol) was added to 6-methoxy-11H-dibenzo[b,f]thiepin-10-one (4.10 g, 16 mmol) in ethylene glycol (20 ml) and the reaction mixture was heated at 175° C. for 3 hours. The reaction mixture was cooled down to room temperature and water was added (100 ml). The white solution was extracted with ether (3×200 ml), the organics were combined, washed with water (100 ml), brine (100 ml) and dried over magnesium sulphate. The solvent was removed in vacuo to give an oil which solidify upon standing to give a brown solid which was used without any further purification (2.45 g, 63%).

Workup

  1. temperatureThe reaction mixture was cooled down to room temperature
  2. extractionThe white solution was extracted with ether (3×200 ml)
  3. washwashed with water (100 ml), brine (100 ml)
  4. dry with materialdried over magnesium sulphate
  5. customThe solvent was removed in vacuo
  6. customto give an oil which
  7. customto give a brown solid which
  8. customwas used without any further purification (2.45 g, 63%)

Sources & evidence

ORD record
ord-1bb8d49370f74bf4862acb3b01efd7f4
Source dataset
uspto-grants-2006_05
Patent number
US07049313B2

Reaction notes

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