Methanol → HCID 21412092, compound

HRID 1284245Notes

Reaction equation

HRID 1284245 reaction equation
[CH3:1][N:2]([CH3:22])[S:3]([C:6]1[CH:7]=[CH:8][C:9]2[CH:15]=[CH:14][C:13]3[CH:16]=[CH:17][CH:18]=[CH:19][C:12]=3[C:11](=[O:20])[C:10]=2[CH:21]=1)(=[O:5])=[O:4].CO.[BH4-].[K+].[OH-].[K+]>O>[CH3:1][N:2]([CH3:22])[S:3]([C:6]1[CH:7]=[CH:8][C:9]2[CH:15]=[CH:14][C:13]3[CH:16]=[CH:17][CH:18]=[CH:19][C:12]=3[CH:11]([OH:20])[C:10]=2[CH:21]=1)(=[O:4])=[O:5]

Participants

6

Reactant 4

HCID 887MethanolHCID 14797Potassium HydroxideHCID 4192641Potassium borohydrideHCID 21412120HCID 21412120, compound

Product 1

HCID 21412092HCID 21412092, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-Dimethylsulfamoyl-5H-dibenzo[a,d]cyclohepten-5-one (6.9 g., 0.022 mole) and 100 ml. of absolute methanol are stirred and heated to refluxing. A solution of 1.6 g. (0.0296 mole) of potassium borohydride in 12 ml. of water containing one pellet of potassium hydroxide is added dropwise at a rate such that reflux is maintained without external heating. After another 11/2 hours at reflux, the solution is evaporated to dryness under reduced pressure. The residual white solid is suspended in water, collected, and crystallized from 95% ethanol. The yield of 3-dimethylsulfamoyl-5H-dibenzo[a,d]cyclohepten-5-ol is 6.05 g. (87%), m.p. 150°-152°C. The melting point is unchanged by further recrystallization.

Workup

  1. temperatureheated to refluxing
  2. temperaturethat reflux
  3. temperatureis maintained without external heating
  4. temperatureAfter another 11/2 hours at reflux
  5. customthe solution is evaporated to dryness under reduced pressure
  6. customcollected
  7. customcrystallized from 95% ethanol
  8. customThe melting point is unchanged by further recrystallization

Sources & evidence

ORD record
ord-5a45eecd61c64d9a9ac4fb21939d9958
Source dataset
uspto-grants-1976_08
Patent number
US03978121

Reaction notes

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