Hydrochloric Acid → HCID 13520250, compound

HRID 485102Notes

Reaction equation

HRID 485102 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[CH2:12][CH2:11][C:10]3[CH:13]=[CH:14][CH:15]=[CH:16][C:9]=3[S:8][C:7]=2[CH:17]=1)#N.Cl.CC[O:21]CC>>[CH:5]1[C:6]2[CH2:12][CH2:11][C:10]3[CH:13]=[CH:14][CH:15]=[CH:16][C:9]=3[S:8][C:7]=2[CH:17]=[C:3]([CH:1]=[O:21])[CH:4]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 13490401HCID 13490401, compound

Product 1

HCID 13520250HCID 13520250, compound

Conditions

Temperature
25 °C

Procedure

Mix 4.74 g (20 mmole) of 3-cyano-10,11-dihydro-dibenzo[b,f]thiepin with 7.56 g (40 mmole) anhydrous stannous chloride and 150 ml ether saturated with anhydrous hydrogen chloride. Stir the mixture at 25° C. for approximately 50 hours to produce a crystalline solid suspended in the reaction mixture. Shake the crystalline solid with 200 ml ice water, and extract with 150 ml ethyl acetate using methanol to dissolve any residual lumpy yellow solid. Separate the ethyl acetate layer containing the product, and after washing with water/saturated chloride solution and drying, the ethyl acetate is removed by evaporation to produce as a residue an amber-colored oil, which crystallizes overnight. Distill the crystalline residue under reduced pressure at 145° C. at 0.04 mm. The distilled product crystallizes, m.p. 55.5°-56.5° C.

Workup

  1. customto produce a crystalline solid
  2. extractionShake the crystalline solid with 200 ml ice water, and extract with 150 ml ethyl acetate
  3. dissolutionto dissolve any residual lumpy yellow solid
  4. customSeparate the ethyl acetate layer
  5. additioncontaining the product
  6. washafter washing with water/saturated chloride solution
  7. customdrying
  8. customthe ethyl acetate is removed by evaporation
  9. customto produce as a residue an amber-colored oil, which
  10. customcrystallizes overnight
  11. distillationDistill the crystalline residue under reduced pressure at 145° C. at 0.04 mm
  12. customThe distilled product crystallizes

Sources & evidence

ORD record
ord-2319d5ca1b004c01a4a16fb85a08f545
Source dataset
uspto-grants-1985_08
Patent number
US04535171

Reaction notes

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