Hydrochloric Acid → Dibenzo[b,f]thiepin-3-carboxaldehyde

HRID 485100Notes

Reaction equation

HRID 485100 reaction equation
Cl.[C:2]([C:4]1[CH:5]=[CH:6][C:7]2[CH:13]=[CH:12][C:11]3[CH:14]=[CH:15][CH:16]=[CH:17][C:10]=3[S:9][C:8]=2[CH:18]=1)#N.[OH2:19]>CCOCC>[CH:6]1[C:7]2[CH:13]=[CH:12][C:11]3[CH:14]=[CH:15][CH:16]=[CH:17][C:10]=3[S:9][C:8]=2[CH:18]=[C:4]([CH:2]=[O:19])[CH:5]=1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 962WaterHCID 13490383HCID 13490383, compound

Product 1

HCID 13520244Dibenzo[b,f]thiepin-3-carboxaldehyde

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

Saturate a suspension of anhydrous stannous chloride (378 mg; 2 mmole) in 7.5 ml dry ether with hydrogen chloride at a temperature of 0°-5° C., and add 235 mg (1 mmole) of 3-cyano-dibenzo[b,f]thiepin. Stir for one hour at 0° C. and allow to warm to room temperature (25° C.). Continue stirring at room temperature for approximately 48 hours. Add 5 ml of water and 1 ml 2N hydrochloric acid, and extract with a mixture of 5 ml ether and 5 ml ethyl acetate. When the hydrolysis of the chloro stannate is complete, evidenced by the disappearance of solids from the solution, separate the organic layer containing the product, wash with water/sodium chloride solution, and after drying, evaporate the solution to produce a dark oil which solidifies when triturated with hexane. The title product is obtained when the above solid material is crystallized from acetonitrile, m.p. 114.5°-115.5° C.

Workup

  1. concentrationSaturate
  2. temperatureto warm to room temperature (25° C.)
  3. stirringContinue stirring at room temperature for approximately 48 hours
  4. extractionextract with a mixture of 5 ml ether and 5 ml ethyl acetate
  5. customWhen the hydrolysis of the chloro stannate
  6. customseparate the organic layer
  7. additioncontaining the product
  8. washwash with water/sodium chloride solution
  9. customafter drying
  10. customevaporate the solution
  11. customto produce a dark oil which
  12. customtriturated with hexane

Sources & evidence

ORD record
ord-43639821fbc44e9a973a8cd7a31486be
Source dataset
uspto-grants-1985_08
Patent number
US04535171

Reaction notes

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