Hydrochloric Acid → 8-Amino-3-cyanodibenzo[b,f]thiepin

HRID 1075002Notes

Reaction equation

HRID 1075002 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[CH:12]=[CH:11][C:10]3[CH:13]=[C:14]([N+:17]([O-])=O)[CH:15]=[CH:16][C:9]=3[S:8][C:7]=2[CH:20]=1)#[N:2].O1CCCC1.Cl.[OH-].[Na+]>O>[NH2:17][C:14]1[CH:15]=[CH:16][C:9]2[S:8][C:7]3[CH:20]=[C:3]([C:1]#[N:2])[CH:4]=[CH:5][C:6]=3[CH:12]=[CH:11][C:10]=2[CH:13]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 131518793-Cyano-8-nitrodibenzo[b,f]thiepin

Product 1

HCID 131518838-Amino-3-cyanodibenzo[b,f]thiepin

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5.6 G. 3-cyano-8-nitrodibenzo[b,f]thiepin is dissolved in 600 cc. tetrahydrofuran and 27 g. stannous chloride dihydrate in 40 cc. water is added, followed by 100 cc. concentrated hydrochloric acid. The mixture is stirred for 24 hours, poured onto ice, and shaken with 300 cc. 20% sodium hydroxide. The organic layer is separated and the aqueous basic layer shaken once more with tetrahydrofuran. The combined organic extracts are dried and the solvent evaporated to dryness and the residue chromatographed on silica gel and eluted with 20% ethyl acetate in benzene to yield 2.45 g. of the pure amine, m.p. 188°-190° C.

Workup

  1. additionpoured onto ice
  2. stirringshaken with 300 cc
  3. customThe organic layer is separated
  4. stirringthe aqueous basic layer shaken once more with tetrahydrofuran
  5. customThe combined organic extracts are dried
  6. customthe solvent evaporated to dryness
  7. customthe residue chromatographed on silica gel
  8. washeluted with 20% ethyl acetate in benzene
  9. customto yield 2.45 g

Sources & evidence

ORD record
ord-691583ce897f4112a6ef913e7767e09b
Source dataset
uspto-grants-1983_07
Patent number
US04394515

Reaction notes

Loading…