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

HRID 362338

Reaction equation

HRID 362338 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-chloroform-ethyl 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-chloroform-ethyl acetate (2:1:1) as solvent
  6. customto give white crystals, m.p. 145°-148° C.

Sources & evidence

ORD record
ord-17e8fc6434d1461c955e3204479e7cfe
Source dataset
uspto-grants-1999_02
Patent number
US05869483

Linked notes

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