Methanol → 10,11-Dihydrodibenzo(b,f)(1,4)thiazepine

HRID 1457622Notes

Reaction equation

HRID 1457622 reaction equation
O=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[S:6][C:5]2[CH:13]=[CH:14][CH:15]=[CH:16][C:4]=2[NH:3]1.B.CSC.CO>O1CCCC1>[CH:9]1[C:8]2[CH2:2][NH:3][C:4]3[CH:16]=[CH:15][CH:14]=[CH:13][C:5]=3[S:6][C:7]=2[CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 374829DibenzothiazepinoneHCID 12423031(Dimethyl sulfide)trihydroboron

Product 1

HCID 1231048210,11-Dihydrodibenzo(b,f)(1,4)thiazepine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 3.3 g of 10,11-dihydro-11-oxodibenz[b,f][1,4]thiazepine in 25 ml of tetrahydrofuran is added 4.0 ml of 10 molar borane-dimethylsulfide in tetrahydrofuran. The mixture is stirred at room temperature for 18 hours, 50 ml of anhydrous methanol added and the solvent removed. An additional 30 ml of methanol is added and the solvent removed to give white crystals. A sample is purified by chromatography on silica gel with hexane-chloroformethyl acetate (2:1:1) as solvent to give white crystals, m.p. 145°-148° C.

Workup

  1. customthe solvent removed
  2. additionAn additional 30 ml of methanol is added
  3. customthe solvent removed
  4. customto give white crystals
  5. customA sample is purified by chromatography on silica gel with hexane-chloroformethyl acetate (2:1:1) as solvent
  6. customto give white crystals, m.p. 145°-148° C.

Sources & evidence

ORD record
ord-bb3ec0c71afe43458f1cf04d0ffd470c
Source dataset
uspto-grants-1998_12
Patent number
US05849735

Reaction notes

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